Herbicidal sulfonamides

ABSTRACT

The novel compounds of Formula I are active as pre-emergent and/or post-emergent herbicides or plant growth regulants. Some of the compounds of the invention show safety to sugarbeets.

CROSS REFERENCE TO RELATED APPLICATION

This application is a continuation-in-part of U.S. Ser. No. 07/193,510which was filed May 12, 1988, and is now abandoned.

BACKGROUND OF THE INVENTION

Herbicidal sulfonylureas are well known in the art. Exemplary of thepatent literature teaching substituted phenyl sulfonylureas are thefollowing: U.S. Pat. Nos. 4,383,113; 4,394,506; 4,478,635; 4,515,626;4,659,369; 4,678,498; 4,705,556; and 4,710,221; EP-A-235,449; and SouthAfrican Patent Applications 84/2722 and 84/5216.

SUMMARY OF THE INVENTION

This application pertains to novel compounds of Formula I,agriculturally suitable compositions containing them and theirmethod-of-use as preemergent and/or postemergent herbicides or plantgrowth regulants. ##STR1## wherein R is H or CH₃ ;

R₁ is NO₂, CO₂ R₄, C(O)R₅, S(O)₂ R₆, ##STR2## R₂ is ##STR3## or CHO; R₃is H, OCH₃, CH₃ or Cl;

R₄ is C₁ -C₃ alkyl, C₂ -C₄ alkoxyalkyl, C₂ -C₃ haloalkyl, allyl orpropargyl;

R₅ is C₁ -C₃ alkyl, C₂ -C₄ alkoxyalkyl, C₃ -C₄ cycloalkyl orcyclopropylmethyl;

R₆ is C₁ -C₃ alkyl or C₂ -C₄ alkoxyalkyl;

R₇ is C₁ -C₃ alkyl, C₂ -C₄ alkoxyalkyl, C₃ -C₄ cycloalkyl,cyclopropylmethyl, C₁ -C₂ alkoxy, CN or Cl;

R₈ is C₁ -C₃ alkyl;

R₉ and R₁₀ are independently C₁ -C₂ alkyl;

R₁₁ is H or CH₃ ;

R₁₂ is H or CH₃ ;

R₁₃ is CN, SCN, NH₂, NHCH₃, N(CH₃)₂, NHC(O)CH₃ or W₂ R₁₆ ;

R₁₄ is C₁ -C₃ alkyl, C₂ -C₄ alkoxyalkyl or C₂ -C₃ haloalkyl;

R₁₅ is H, C₁ -C₃ alkyl, C₂ -C₄ alkoxyalkyl or C₂ -C₃ haloalkyl;

R₁₆ is H, C₁ -C₆ alkyl, C₃ -C₄ cycloalkyl or C₄ -C₅ cycloalkylalkyl;

W₂ is O or S;

X is C₁ -C₂ alkyl, OCH₃, Cl, or OCF₂ H;

Y is H, CH₃, C₁ -C₂ alkoxy, NHCH₃, or N(CH₃)₂ ; and

Z is CH or N;

and their agriculturally suitable salts; provided that

1) when X is Cl, then Z is CH and Y is OCH₃, OC₂ H₅, NHCH₃, or N(CH₃)₂ ;

2) when X is OCF₂ H, then Z is CH and R₂ is ##STR4## 3) when R₂ is##STR5## then R₁ is CO₂ R₄ ; 4) When R₁₆ is H, W₂ is O.

In the above definitions, the term "alkyl, " used either alone or incompound words such as "alkoxyalkyl" or "haloalkyl, " includes straightchain or branched alkyl, e.g., methyl, ethyl, n-propyl or isopropyl.

Alkoxy includes methoxy, ethoxy, n-propyloxy and isopropyloxy.

Alkoxyalkyl includes methoxymethyl through the different methoxypropyland propyloxymethyl isomers.

Cycloalkyl includes cyclopropyl and cyclobutyl.

C₄ -C₅ cycloalkylalkyl means cyclopropylmethyl through cyclopropylethylor cyclobutylmethyl.

The term "halogen," either alone or in compound words such as"haloalkyl," means fluorine, chlorine, bromine or iodine. Further, whenused in compound words such as "haloalkyl," said alkyl may be partiallyor fully substituted with halogen atoms, which may be the same ordifferent. Examples of haloalkyl include CH₂ CH₂ F, CF₂ CF₃ and CH₂CHFCl.

The total number of carbon atoms in a substituent group is indicated bythe C_(i) -C_(j) prefix where i and j are numbers from 1 to 5. Forexample, C₁ -C₃ alkyl would designate methyl through the propyl isomers;C₂ alkoxyalkyl would designate CH₂ OCH₃ ; C₄ alkoxyalkyl would designatethe various isomers of an alkyl group substituted with a alkoxy groupcontianing a total of 4 carbon atoms, examples including but not limitedto CH₂ OCH₂ CH₂ CH₃, CH₂ OCH(CH₃)₂, CH(CH₃)OCH₂ CH₃, CH(CH₂ CH₃)OCH₃,CH₂ CH₂ OCH₂ CH₃ and CH₂ CH₂ CH₂ OCH₃.

Preferred compounds for reasons of increased ease of synthesis and/orgreater herbicidal efficacy are:

1) Compounds of Formula I where

R is H; and

R₃ is H.

2) Compounds of Preferred 1 where

R₄ is CH₃, CH₂ CH₃ or CH₂ OCH₃ ;

R₅ is C₁ -C₃ alkyl, cyclopropyl, cyclopropylmethyl or CH₂ OCH₃ ;

R₆ is C₁ -C₃ alkyl or CH₂ OCH₃ ;

R₇ is C₁ -C₃ alkyl, cyclopropyl, cyclopropylmethyl or CH₂ OCH₃ ; and

R₁₆ is H, or C₁ -C₃ alkyl.

3) Compounds Preferred 2 where R₂ is ##STR6## 4) Compounds of Preferred3 where R₁₃ is W₂ R₁₆.

5) Compounds of Preferred 2 where

R₂ is NHR₁₄.

6) Compounds of Preferred 2 where

R₂ is ##STR7## 7) Compounds of Preferred 2 where R₂ is CHO.

Specifically preferred for reasons of greatest ease of synthesis and/orgreatest herbicidal efficacy and/or greatest safety to sugar beets are:

Methyl2-[[[[(4,6-dimethoxypyrimidin-2-yl)amino]carbonyl]amino]sulfonyl]-5-(methoxymethyl)benzoate,m.p. 182°-184° C.; and

Methyl 2-[[[[(4,6-dimethoxypyrimidin-2-yl)amino]carbonyl]amino]sulfonyl]-5-(hydroxymethyl)benzoate,m.p. 182°-185° C.

DETAILED DESCRIPTION OF THE INVENTION Synthesis

The preparation of compounds of Formula I can be accomplished using awide variety of methods well known in the art. Some of the more generalmethods used to prepare these materials are described below in Equations1 and 2.

Many of the compounds of Formula I can be prepared by the couplingreaction of sulfonyl isocyanates of Formula II with heterocyclic aminesof Formula III as shown below in Equation 1. Equation 1 ##STR8##wherein, R, R₁ R₃, X, Y and Z are as previously defined;

R₂ is ##STR9## R₁₃ is CN, SCN, W₂ R₁₆ ; and W₂, R₁₂, R₁₃ and R₁₆ are aspreviously defined.

A useful reference for this coupling reaction is found in U.S. Pat. No.4,394,506.

Sulfonyl isocyanates of Formula II can be prepared both from thecorresponding sulfonamides of Formula V and the corresponding sulfonylchloride of Formula VI using methods well known in the art. For a fewrepresentative examples of this process see: U.S. Pat. No. 4,238,621;Ulrich and Sayigh, Newer Methods of Preparative Organic Chemistry, Vol.VI, pp. 223-241, Academic Press, New York and London, W. Roerst, Ed.;Japanese Patent No. 76/126,816; U.S. Pat. No. 4,394,506; and K. Kartke,Arch. Pharm., 299, 174 (1966).

A number of compounds of Formula I can be prepared by the reaction ofN-phenylcarbamate derivatives of sulfonamides of Formula V withheterocyclic amines of Formula III. This method and the generalprocedure for the preparation of sulfonyl carbamates is taught in U.S.Pat. No. 4,443,245.

Compounds of Formula I can be prepared by the base catalyzed reaction ofsulfonamides of Formula V (R_(a) is H) with phenyl carbamates of FormulaVII. This general method is widely described in the literature and alead reference is found in EPO Publication No. 44807. Alternatively,compounds of Formula I can be prepared by the fluoride ion catalyzedcoupling of N-t-butyldimethylsilyl derivatives of sulfonamides ofFormula V (R_(a) is t-butyldimethylsilyl) with phenyl carbamates ofFormula VII as taught in U.S. Pat. No. 4,666,501 (Equation 2). ##STR10##wherein, R, R₁, R₂, R₃, X, Y and Z are as previously defined.

With the diversity of functional groups R₁, R₂ and R₃ found in thisinvention, a variety of methods can be used for the preparation of thenumerous combinations of R₁, R₂ and R₃. Fortunately, there are a vastnumber of general synthetic methods available in the literature thatenable the preparation of these compounds. With this wealth ofinformation, one skilled in the art would be able to discern the mostappropriate synthetic method by taking into account the chemicalcompatability of the various groups with the reaction conditions.

Sulfonamides of Formula V can be prepared using a variety of methodswell known in the art. One of the most direct preparations is thereaction of ammonia with sulfonyl chlorides of Formula VI with fullyassembled R₁, R₂ and R₃ substituents. For two useful reviews see, F.Hawking and J. S. Lawrence, "The Sulfonamides." H. K. Lewis and Co.,London, 1950 and E. H. Northey, "The Sulfonamides and Allied Compounds,"Reinbold Publishing Corp., New York, 1948. These intermediates can thenbe used to prepare compounds of Formula I as described in Equation 2.

Sulfonyl chlorides of Formula VI with less elaborated R₁, R₂ and R₃substituents can be either aminated with t-butylamine to produceN-t-butyl sulfonamides of Formula V (R_(a) is t-butyl) (Equation 3a) orby ammonia followed by silylation to produce N-t-butyldimethylsilylsulfonamides of Formula V (R_(a) is t-butyldimethylsilyl) (Equation 3b).Both of these derivatives are useful intermediates which allow furthermodifications of the R₁, R₂ and R₃ substituents. ##STR11## wherein R₁,R₂ and R₃ are as previously defined.

After the R₁, R₂ and R₃ substituents have been assembled in theN-substituted sulfonamides of Formula V (R_(a) is t-butyl ort-butyldimethylsilyl) these compounds are ready to be converted into thecompounds of Formula I. The N-silylated sulfonamides of Formula V (R_(a)is t-butyldimethylsilyl) can be used directly as described in Equation2. While the N-t-butyl sulfonamides require deprotection by the actionof trifluoroacetic acid before they can be taken on as described inEquation 2. The deprotection of these N-t-butyl sulfonamide derivativesis known in the literature and for an appropriate reference see: J. D.Catt and W. L. Matier, J. Org. Chem., 39, 566 (1974).

A few of the strategies used to elaborate the ring substituents of theN-substituted sulfonamide derivatives of Formula V (R_(a) is t-butyl ort-butyldimethylsilyl) into the more complicated R₁, R₂ and R₃ groups areshown below in Equations 4 to 7.

In terms of the R₂ substituents, three basic methods can be used toproduce sulfonamides of Formula V:

A) From 4-methyl and ethyl precursors,

B) From 4-nitro precursors,

C) From 4-halo precursors.

A) From 4-methyl and ethyl precursors:

Most of the sulfonamides of Formula V in which the R₂ substituents aresubstituted methyl or ethyl groups are derived from the nucleophilicdisplacement reaction of benzylic halides (or equivalent group) ofFormula Vb and an appropriate nucleophile (Equation 4a). This type ofprocess is extensively described in the literature, for references see:Hartshorn, "Aliphatic Nucleophilic Substitution," Cambridge UniversityPress, Cambridge, 1973; Bunton, "Nucleophilic Substitutions at aSaturated Carbon Atom," American Elsevier Publishing Company, New York,1963; and de la Mare and Swedlund, in Patai, "The Chemistry of theCarbon-Halogen Bond," pt. 1, pp. 409-490, John Wiley & Sons, New York1973; Parker, Adv. Org. Chem., 5, (1965) 1-46. ##STR12## wherein, R₁ andR₃ are as previously defined;

R_(a) is H, t-butyl or t-butyldimethylsilyl;

X₁ is Cl, Br, I, OSO₂ Ph--4--CH₃ or OSO₂ CH₃ ;

R_(b) is H or CH₃ ;

R₂ is ##STR13## and R₁₂ and R₁₃ are as previously defined.

The benzylic halides, tosylates or mesylates of Formula Vb can bereadily prepared from sulfonamides of Formula Va using any one of anumber of standard techniques (Equation 4b). Some useful references canbe found in: Nechvatal, Adv. Free-Radical Chem., 4, 175-201 (1972);Novikov, Sevost'yanova, and Fainzil'berg, Russ. Chem. Rev., 31, 671-681(1962); Horner and Winkelmann, Newer Methods Prep. Org. Chem., 3,151-198 (1964), pp. 674-677; Djerassi, Chem. Rev., 43, 271-317 (1948).

B) From 4-nitro precursors:

Sulfonamides of Formula V with R₂ substituents comprised of amine orhydroxylamine derivatives can be prepared from the corresponding 4-nitrosulfonamides of Formula Vc. In these cases, the 4-nitro group can beeasily reduced to furnish the corresponding amine or hydroxylaminedepending on reaction conditions. For a lead reference concerning thesetypes of reductions see: March, "Advanced Organic Chemistry," pp.1125-1126, McGraw-Hill, Inc., New York 1977; J. S. Buck and W. S. Ide,Org. Syn., Coll. Vol., 1, 130 (1943). These key intermediates can thenbe derivatized using methods known by one skilled in the art to furnishthe desired sulfonamides of Formula V (Equation 5). A good reference forthese derivatizing methods is: Greene, "Protective Groups in OrganicSynthesis," John Wiley and Sons, New York (1981). ##STR14## wherein, R₃is as previously defined;

R_(a) is H, t-butyl or t-butyldimethylsilyl;

R₂ is --NHR₁₄, or --N(R₁₅)OH, R₁₄ and R₁₅ are as previously defined;

R₁ is CO₂ R₄ ; and

R₄ is as previously defined.

C) From 4-halo precursors:

Halogens, such as F, Cl or Br, substituted in the 4-position ofsulfonamides of Formula Vd are susceptible to nucleophilic displacementreactions. In some cases, it is advantageous to use this strategy toprepare sulfonamides of Formula V with amine or hydroxylaminederivatives as the R₂ substituent (Equation 6). This type of reaction isknown in the art and for reference see: Zoltewicz, Top. Curr. Chem., 59,33-64 (1975); Bunnett and Zahler, Chem. Rev., 49, 273-412 (1951); Millerand Parker, Aust. J. Chem., 11, 302 (1958); Berliner and Monack, J.Amer. Chem. Soc., 74, 1574 (1952). ##STR15## wherein, R₃ is aspreviously defined;

R_(a) is H, t-butyl or t-butyldimethylsilyl;

X₂ is F, Cl or Br;

R₂ is NHR₁₄ or N(R₁₅)OH;

R₁₄ and R₁₅ are as previously defined; and

R₁ is CO₂ R₄ and R₄ is as previously defined.

Many of the R₁ substituents found in sulfonamides of Formula V can beprepared from sulfonamides of Formula Ve (R_(a) is t-butyl ort-butyldimethylsilyl) where R₁ is hydrogen. In these cases, the positionortho to the protected sulfonamide group can be deprotonated by theaction of strong base. The resultant dianion can then be quenched with avariety of electrophiles which either furnish the requisite R₁substituents directly or furnish precursors to these key groups. Thissequence of reaction is well documented in the literature and thefollowing references describe this technique: J. G. Lombardino, J. Org.Chem., 36, (1971), 1843; P. Beak and R. A. Brown, J. Org. Chem., 44,(1979) 4464; and P. Beak and V. Snieckus, Acc. Chem. Res., 15, (1982)306.

This method works well for the preparation of sulfonamides of Formula Vein which the 4-substituent is methyl, ethyl, Cl or F (Equation 7a). Incases where the electrophile is a chloroformate derivative, and anexcess of the electrophile is used, saccharin derivatives of FormulaVIII (where R_(a) is either H or t-butyl) can be obtained as the onlyproduct (Equation 7b). The ring substituents on these saccharinderivatives can be modified to the desired R₁, R₂ and R₃ groups in muchthe same manner as the ring opened sulfonamides of Formula Va and d asdescribed in Equations 4 and 6. In addition, these saccharin derivativescan be easily converted into the sulfonamides of Formula V (R_(a) is Hor t-butyl) by methods well known in the art. ##STR16## wherein, R₃ isas previously defined;

R_(a) is t-butyl or t-butyldimethylsilyl;

R_(c) is F, Cl, CH₃ or CH₂ CH₃ ;

Vd is as defined in Equation 6;

Va is as defined in Equation 4;

R'_(a) is H or t-butyl; and

R₁ is as previously defined excluding: ##STR17##

There are a variety of additional general methods in the literature thatcan be used for the preparation of many of the sulfonyl chlorides ofFormula VI and sulfonamides of Formula V (R_(a) is H, t-butyl ort-butyldimethylsilyl). Some representative methods are described in: H.T. Clarke et al., Org. Synth. Coll., Vol. 1, 2nd Ed. 1941, p. 85; H. L.Tale and F. Sowinski, J. Org. Chem., 25, 1824 (1960); and H. Meerwein etal., Chem. Ber., 90, 841 (1957). Additional references can be found inU.S. Pat. Nos. 4,169,719; 4,127,405; 3,394,506; 4,435,205; 4,420,325;4,441,910; 4,398,939; 4,456,469; 4,370,479; and EPO Publications Nos.:23,422; 83,975; 13,480 and 95,925.

Equations 8 to 11 describe a number of specific synthetic schemes thatenable the preparation of a variety of sulfonyl chlorides of Formula VI.These intermediates can then be; 1) converted directly into compounds ofFormula I using procedures outlined above; 2) converted intosulfonamides of Formula V (R_(a) is H) which in turn to compounds ofFormula I; and, 3) converted into sulfonamides of Formula V (R_(a) ist-butyl or t-butyldimethylsilyl) for further manipulations using methodsalready described to furnish the required R₁, R₂ and R₃ substituents.

From amino (or nitro) precursors:

A number of sulfonyl chlorides of Formula VIa where the ringsubstituents are compatible with the variety of conditions used togenerate diazonium salts can be prepared from the corresponding aminoderivative of Formula IX as taught in U.S. Pat. No. 4,310,346 (Equation8). The amino derivatives of Formula IX can be obtained commercially orprepared from the corresponding nitro compounds by any one of manymethods known in the literature. ##STR18## wherein, R₁ is H or aspreviously defined;

R₃ is as previously defined;

R₂ can be CH₃, CH₂ CH₃, Cl, F, Br, NO₂ and as previously defined except,not NHR₁₄, N(R₁₅)OH and R₁₃ is not NH₂, NHCH₃, or N(CH₃)₂ ; and

W₂ is not S.

From halogen precursors:

A number of sulfonyl chlorides of Formula VIb in which the ringsubstituents are compatible with the conditions associated with theoverall process of nucleophilic displace of an activated halogen withthiolate ions followed by oxidative chlorination can be prepared fromthe corresponding aryl halides of Formula X (Equation 9). This sequenceis taught in EPO Publication No. 94,821. ##STR19## wherein, R₁ is H orpreviously defined except not, C(O)R₅, ##STR20## R₂ is NO₂, CH₃, CH₂CH₃, Cl; R₃ is as previously defined; and

X₃ is F, Cl or Br.

From phenol precursors:

Sulfonyl chlorides of Formula VIc in which the ring substituents are notcompatable with nucleophilic displacement reactions or oxidativechlorination conditions can be prepared from the corresponding phenol ofFormula XI (Equation 10). A lead reference for this sequence is M. S.Newman and H. A. Kames, J. Org. Chem., 31 (1966), 3980. ##STR21##wherein, R₁ is H or as previously described except;

R₇ is not C₁ -C₂ alkoxy, CN or Cl;

R₂ is NO₂, CH₃, CH₂ CH₃, Cl or Br; and

R₃ is as previously defined.

From aryl bromides:

Sulfonyl chlorides of Formula VId in which the ring substituents arestable to strong bases can be prepared using a sequence starting withthe corresponding aryl bromides or the parent protio compound of FormulaXII (Equation 11). These reactions have been extensively studies in theliterature and a few lead references for this useful process can befound in: U.S. Pat. No. 4,481,029; Gschwend and Rodriguez, Org.Reactions, 26 (1979), 1; S. N. Bhattacharya et al., J. Chem. Soc. C.,(1968), 1265. ##STR22## wherein, R₁ is H or as previously defined exceptfor NO₂, CO₂ R₄, C(O)R₅ ; and

R₇ is not C₁ -C₂ alkoxy, CN or Cl;

R₂ is Cl, F, CH₃ or CH₂ CH₃ ;

R₃ is as previously defined; and

X₄ is H or Br.

Another useful preparation of sulfonyl chlorides of Formula VI is byelectrophilic chlorsulfonation of a suitably substituted aromatic ring.This technique is well known in the literature and works best for alkylaryl ethers and alkyl aromatics. A useful reference is E. H. Huntressand F. H. Carten, J. Am. Chem. Soc., 62 (1940), 511-14 and 603-4.

The heterocyclic amines of Formula III are either known or can beprepared by obvious methods by one skilled in the art.

For a review of the synthesis and reactions of 2-amino and2-methylaminopyrimidines (III, Z=CH) see The Chemistry of HeterocyclicCompounds, Vol. 16, Wiley-Interscience, New York (1962). For a review ofthe synthesis and reactions of 2-amino- and 2-methylamino-s-triazines(III, Z=N) see The Chemistry of Heterocyclic Compounds, Vol. 13,Wiley-Interscience, New York (1959), F. C. Schaefer, U.S. Pat. No.3,154,537 and F. C. Schaefer and K. R. Huffman, J. Org. Chem., 28, 1812(1963). Heterocyclic amines, wherein X or Y is OCF₂ H, may be preparedas described in U.S. Pat. No. 4,478,635.

The preparation of the compounds of this invention is furtherillustrated by the following Examples.

EXAMPLE 1 N-t-butyl 1,2-benzisothiazole-3-2H/-one 5-methyl-1,1-dioxide

To 4-methyl N-t-butylbenzenesulfonamide (10 g, 0.044 mol) in drytetrahydrofuran (THF) (250 mL) cooled to -78° C. was added dropwisen-butyllithium (35.2 mL, 2.5M, 0.088 mol) at such a rate that thetemperature was kept below -65° C. After all the n-butyllithium solutionwas added the mixture was warmed to 35° C. with a warm water bath andthe mixture stirred for 2 hours. The heterogeneous mixture was thenre-cooled to 31 78° C. and methyl chloroformate (10.2 mL, 0.132 mol) wasadded as rapidly as possible and the mixture was allowed to warm to roomtemperature. Upon warming, the mixture became homogeneous and wasallowed to stirred an additional hour.

The reaction was worked-up by adding distilled water and adjusting thepH to approximately 3 using 1.0N HCl. The layers were separated and theaqueous layer was extracted with a mixture of diethyl ether and ethylacetate. The organic layers were combined, washed with brine and driedusing magnesium sulfate. The solvents were removed by rotary evaporationto leave 12.45 g of a free-flowing white solid; m.p. 85° to 88° C., andone spot by TLC.

NMR (200 MHz) CDCl₃ δ 7.75 (d, 1H), 7.7 (d, 1H), 7.6 (dd, 1H), 2.5 (s,3H), 1.8 (s, 9H).

This was deemed pure enough for the next step.

EXAMPLE 2 Methyl 2-(N-t-butylsulfonyl)-5-(methoxymethyl)benzoate

The N-t-butyl saccharin derivative from Example 1 (10 g, 0.39 mol) wasdissolved in a mixture of CCl₄ (250 mL) and CH₂ Cl₂ (100 mL). ThenN-bromosuccinimide (9.43 g, 0.53 mol) was added and the mixture washeated at reflux for approximately 2 hours after which time it wascooled to room temperature and allowed to stir for 12 hours. Thereaction mixture was again heated at reflux but this time with the aidof a sun lamp. After 2 hours, the reaction was deemed complete and themixture was concentrated on a rotary evaporator.

The residue was dissolved in diethyl ether and was immediately washedwith an aqueous 5% sodium bisulfite solution. The ether layer was driedusing magnesium sulfate, filtered and concentrated on a rotaryevaporator to furnish 14.3 g of the crude product as a brown oil. Thismaterial was used in the next step without further purification.

This crude reaction mixture (12.17 g) was dissolved in methanol (150 mL)and then treated with a 25% sodium methoxide solution in methanol (20.44mL) and the mixture was allowed to stir for 1 hour at 25° C. TLCanalysis indicated that the reaction was incomplete so it was heated at50° C. for approximately 2 hours. At the end of this time, the reactionwas judged to be complete and the mixture was concentrated on a rotaryevaporator to give a heterogeneous brown oil. The mixture was dilutedwith water and acidified with 1N HCl and the aqueous layer was extractedwith diethyl ether. The organic layer was dried using magnesium sulfate,filtered and concentrated to furnish 8.66 g of a brown oil. Thismaterial was chromatographed on silica gel using a solvent system ofethyl acetate and hexane (1:9). This yielded 1.60 g of desired productas a white solid; m.p. 70°-72° C.

NMR (200 MHz) CDCl₃ δ 8.1 (d, 1H), 7.8 (s, 1H), 7.6 (d, 1H), 6.1 (bs,1H), 4.5 (s, 2H), 4.0 (s, 3H), 3.4 (s, 3H), 1.3 (s, 9H).

EXAMPLE 3 Methyl 1-(aminosulfonyl)-5-(methoxymethyl)benzoate

The N-t-butylsulfonamide (1.6 g) prepared in Example 2 was dissolved intrifluoroacetic acid (10 mL) at 0° C. and the mixture was allowed tostir while warming to room temperature. The mixture was allowed to stirovernight after which time the trifluoroacetic acid was removed on arotary evaporator. The crude oil was repeatedly dissolved in heptane andconcentrated in vacuo to furnish a gray-brown tacky solid. The solid wastriturated with n-chlorobutane and the desired product was collected asan off-white solid; m.p. 110°-115° C.

NMR (100 MHz) D₆ acetone δ 8.0 (dd, 1H), 7.8 (s, 1H), 7.7 (d, 1H), 6.6(bs, 1H), 4.6 (s, 1H), 4.0 (s, 3H), 3.4 (s, 3H).

EXAMPLE 4 Methyl2-[[[[(4,6-dimethoxypyrimidin-2-yl)amino]carbonyl]amino]sulfonyl]-5-(methoxymethyl)benzoate

The sulfonamide prepared in Example 3 (100 mg, 0.386 mmol) and phenyl4,6-dimethoxypyrimidin-2-yl carbamate (106 mg, 0.386 mmol) weredissolved in dry acetonitrile (2 mL) and cooled to 0° C. Then1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.07 mL, 0.463 mmol) was addedand the mixture stirred for 1 hour. After this time ice and water wereadded and the solution was acidified to pH 3 with 1N HCl. The resultantsolids were collected, washed with water and air dried to yield 0.145 gof a white solid that melted at 182°-184° C.

NMR (200 MHz) D₆ acetone δ 12.6 (bs, 1H), 9.4 (bs, 1H), 8.3 (d, 1H), 7.7(m, 2H), 5.9 (s, 1H), 4.05 (s, 6H), 3.9 (s, 3H), 3.4 (s, 3H).

EXAMPLE 5 N-t-butyl 1,2-benzisothiazole-3-2H/-one5-acetoxymethyl-1,1-dioxide

Silver acetate (7.5 g) was suspended in acetonitrile (50 mL) and aceticacid (30 mL) was added until the mixture became homogeneous. Then asample of 5-bromomethyl-N-t-butylsaccharin (5.0 g) (prepared asdescribed in Example 2) was added in acetonitrile (40 mL) and themixture was allowed to stir for 4 days at room temperature. The mixturewas filtered and the filtrate was diluted with water and extracted withethyl acetate (3×150 mL). The ethyl acetate solutions were combined andwashed once with water and then once with saturated sodium bicarbonatesolution. The organics were dried with magnesium sulfate, filtered andconcentrated to furnish 4 g of yellow oil which crystallized uponstanding. This material was chromatographed on silica gel first usingethyl acetate and hexane (1:8) as eluent followed by a 1:1 mixture. Thedesired product 1.7 g was obtained as a white solid that melted at106°-108° C.

NMR (90 MHz) CDCl₃ δ 7.9 (s, 1H), 7.7 (s, 2H), 5.2 (s, 2H), 2.1 (s, 3H),1.7 (s, 9H).

EXAMPLE 6 Methyl 2-(N-t-butylsulfonyl)-5-(hydroxymethyl)benzoate

The 5-acetoxymethyl saccharin (1.7 g) prepared in Example 5 wasdissolved in methanol (20 mL) and a 25% sodium methoxide in methanolsolution (1.5 mL) was added and the mixture was allowed to stir for 12hours. After this time, the mixture was poured onto an ice and watermixture and the resultant solution was extracted with ethyl acetate(3×50 mL). The organics were dried with magnesium sulfate, filtered andconcentrated to afford 1.3 g of the desired product initially as a clearoil which slowly solidified on standing.

NMR (90 MHz) CDCl₃ δ 8.0 (d, 1H), 7.9 (d, 1H), 7.7 (dd, 1H), 6.1 (bs,1H), 4.8 (d, 2H), 4.0 (s, 3H), 2.7 (t, 1H), 1.4 (s, 9H),

EXAMPLE 7 Methyl 2-(aminousulfonyl)-5-(hydroxymethyl)benzoate and Methyl2-(aminosulfonyl)-5-(trifluoroacetoxymethyl)benzoate

Using the same procedure described in Example 3, the N-t-butylsulfonamide (1.2 g) prepared in Example 6 was deprotected withtrifluoroacetic acid (10 mL). This furnished 1.05 g of a white solid;m.p. 98°-100° C. The solid was a mixture of the desired hydroxymethylsulfonamide and its corresponding trifluoroacetate.

NMR (200 MHz) D₆ Acetone δ 8.15 (d, 1H), 7.95 (d, 1H), 7.9 (dd, 1H), 6.5(bs, 2H), 5.6 (CH₂ OCOCF₃), and 4.8 (CH₂ OH) (s, 2H), 4.0 (s, 3H).

This mixture was used as is as trifluoroacetates such as these arecleaved during the next step.

EXAMPLE 8 Methyl2[[[[(4,6-dimethoxypyrimidin-2-yl)amino]carbonyl]amino]sulfonyl]-5-(hydroxymethyl)benzoate

Using the same procedure described in Example 4, the mixture ofsulfonamides (0.1 g) produced the desired product (0.1 g) (in which thetrifluoroacetate had indeed been hydrolyzed) as a white solid; m.p.182°-185° C.

NMR (200 MHz) D₆ Acetone δ 12.6 (bs, 1H), 9.4 (bs, 1H), 8.3 (d, 1H), 7.7(m, 2H), 5.9 (s, 1H), 4.8 (s, 2H), 4.05 (s, 6H), 3.9 (s, 3H).

Using the methods described above in Equations 1 to 11, the methods (ormodifications thereof) referred to by reference and Examples 1 to 8, oneskilled in the art can prepare the following compounds in Tables 1 to13. ##STR23##

                  TABLE 1                                                         ______________________________________                                        Formula I                                                                     R.sub.1                  R.sub.13                                             ______________________________________                                        NO.sub.2                 OH                                                   CO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                                     OCH.sub.3                                            CO.sub.2 CH(CH.sub.3).sub.2                                                                            OH                                                   CO.sub.2 CH.sub.2 OCH.sub.3                                                                            OCH.sub.3                                            CO.sub.2 (CH.sub.2).sub.2 OCH.sub.3                                                                    OCH.sub.3                                            CO.sub.2 (CH.sub.2).sub.2 OCH.sub.2 CH.sub.3                                                           OCH.sub.3                                            CO.sub.2 (CH.sub.2).sub.2 Cl                                                                           OCH.sub.3                                            CO.sub.2 (CH.sub.2).sub.2 Br                                                                           OCH.sub.3                                            CO.sub.2 (CH.sub.2).sub.3 F                                                                            OCH.sub.3                                            CO.sub.2 CH.sub.2 CHCH.sub.2                                                                           OCH.sub.3                                            CO.sub.2 CH.sub.2 CCH    OCH.sub.3                                            C(O)CH.sub.3             OH                                                   C(O)CH.sub.2 CH.sub.3    OH                                                   C(O)(CH.sub.2).sub.2 CH.sub.3                                                                          OH                                                   C(O)CH(CH.sub.3).sub.2   OH                                                   C(O)CH.sub.2 OCH.sub.3   OH                                                   C(O)CH.sub.2 OCH.sub.2 CH.sub.3                                                                        OCH.sub.3                                            C(O)CH(CH.sub.3)OCH.sub.3                                                                              OCH.sub.3                                            C(O)CH(CH.sub.3)OCH.sub. 2 CH.sub.3                                                                    OCH.sub.3                                            C(O)CH.sub.2 CH.sub.2 F  OCH.sub.3                                            C(O)(CH.sub.2).sub.2 CH.sub.3                                                                          OCH.sub.3                                            C(O)(CH.sub.2).sub.2 CH.sub.3                                                                          OH                                                   SO.sub.2 CH.sub.3        OH                                                   SO.sub.2 CH.sub.2 CH.sub.3                                                                             OCH.sub.3                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                                     OCH.sub.3                                            SO.sub.2 CH.sub.2 OCH.sub.3                                                                            OCH.sub.3                                            SO.sub.2 (CH.sub.2).sub.2 OCH.sub.3                                                                    OCH.sub.3                                            SO.sub.2 CH.sub.2 OCH.sub.2 CH.sub.3                                                                   OCH.sub.3                                            C(CH.sub.3)(NOCH.sub.3)  OH                                                   C(CH.sub.2 CH.sub.3)(NOCH.sub.3)                                                                       OH                                                   C(OCH.sub.3)(NOCH.sub.3) OCH.sub.3                                            C(OCH.sub.2 CH.sub.3)(NOCH.sub.3)                                                                      OCH.sub.3                                            C(CN)(NOCH.sub.3)        OCH.sub.3                                            C(Cl)(NOCH.sub.3)        OCH.sub.3                                            C(CH.sub.3)(NOCH.sub.2 CH.sub.3)                                                                       OCH.sub.3                                            C(CH.sub.3)(NO(CH.sub.2).sub.2 CH.sub.3)                                                               OCH.sub.3                                            C(CH.sub.3)(OCH.sub.3).sub.2                                                                           OH                                                   CH(OCH.sub.3).sub.2      OCH.sub.3                                            CH(OCH.sub.2 CH.sub.2 O).sub.2                                                                         OCH.sub.3                                            CH(OCH(CH.sub.3)CH.sub.2 O).sub.2                                                                      OCH.sub.3                                            ______________________________________                                    

                  TABLE 2                                                         ______________________________________                                         ##STR24##                                                                    Formula 2                                                                     R.sub.4         R.sub.2                                                       ______________________________________                                        CH.sub.3        CH.sub.2 CN                                                   CH.sub.3        CH(CH.sub.3)CN                                                CH.sub.3        CH.sub.2 SCN                                                  CH.sub.3        CH(CH.sub.3)SCN                                               CH.sub.3        CH.sub.2 NH.sub.2                                             CH.sub.3        CH.sub.2 NHCH.sub.3                                           CH.sub.3        CH.sub.2 N(CH.sub.3).sub.2                                    CH.sub.3        CH.sub.2 NHCOCH.sub.3                                         CH.sub.3        CH(CH.sub.3)NHCOCH.sub.3                                      CH.sub.3        CH.sub.2 OH                                                   CH.sub.3        CH(CH.sub.3)OH                                                CH.sub.3        CH.sub.2 OCH.sub.3                                            CH.sub.3        CH.sub.2 OCH.sub.2 CH.sub.3                                   CH.sub.3        CH.sub.2 O(CH.sub.2).sub.2 CH.sub.3                           CH.sub.3        CH.sub.2 O(CH.sub.2).sub.3 CH.sub.3                           CH.sub.3        CH.sub.2 O(CH.sub.2).sub.4 CH.sub.3                           CH.sub.3        CH.sub.2 OCH.sub.2 (CH.sub.2).sub.4 CH.sub.3                  CH.sub.3        CH.sub.2 SCH.sub.3                                            CH.sub.3        CH.sub.2 SCH.sub.2 CH.sub.3                                   CH.sub.3        CH.sub.2 SCH(CH.sub.3).sub.2                                  CH.sub.3        CH.sub.2 SCH.sub.2 (CH.sub.2).sub.3 CH.sub.3                  CH.sub.3        NHCH.sub.3                                                    CH.sub.3        NHCH.sub.2 CH.sub.3                                           CH.sub.3        NH(CH.sub.2).sub.2 CH.sub.3                                   CH.sub.3        NHCH(CH.sub.3).sub.2                                          CH.sub.3        NHCH.sub.2 OCH.sub.3                                          CH.sub.3        NH(CH.sub.2).sub.2 OCH.sub.3                                  CH.sub.3        NH(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3                         CH.sub.3        NHCH.sub.2 CF.sub.3                                           CH.sub.3        NHCH(CH.sub.3)CH.sub.2 OCH.sub.3                              CH.sub.3        N(OH)H                                                        CH.sub.3        N(OH)CH.sub.3                                                 CH.sub.3        N(OH)CH.sub.2 CH.sub.3                                        CH.sub.3        N(OH)CH(CH.sub.3).sub.2                                       CH.sub.3        N(OH)(CH.sub.2).sub.2 CH.sub.3                                CH.sub.3        N(OH)CH.sub.2 CF.sub.3                                        ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                         ##STR25##                                                                    Formula 3                                                                     R.sub.4         R.sub.2                                                       ______________________________________                                        CH.sub.3        CH.sub.2 CN                                                   CH.sub.3        CH(CH.sub.3)CN                                                CH.sub.3        CH.sub.2 SCN                                                  CH.sub.3        CH(CH.sub.3)SCN                                               CH.sub.3        CH.sub.2 NH.sub.2                                             CH.sub.3        CH.sub.2 NHCH.sub.3                                           CH.sub.3        CH.sub.2 N(CH.sub.3).sub.2                                    CH.sub.3        CH.sub.2 NHCOCH.sub.3                                         CH.sub.3        CH(CH.sub.3)NHCOCH.sub.3                                      CH.sub.3        CH.sub.2 OH                                                   CH.sub.3        CH(CH.sub.3)OH                                                CH.sub.3        CH.sub.2 OCH.sub.3                                            CH.sub.3        CH.sub.2 OCH.sub.2 CH.sub.3                                   CH.sub.3        CH.sub.2 O(CH.sub.2).sub.2 CH.sub.3                           CH.sub.3        CH.sub.2 O(CH.sub.2).sub.3 CH.sub.3                           CH.sub.3        CH.sub.2 O(CH.sub.2).sub.4 CH.sub.3                           CH.sub.2 CH.sub.3                                                                             CH.sub.2 OCH.sub.2 (CH.sub.2).sub.3 CH.sub.3                  CH.sub.3        CH.sub.2 OCH.sub.2 (CH.sub.2).sub.4 CH.sub.3                  CH.sub.3        CH.sub.2 SCH.sub.3                                            CH.sub.3        CH.sub.2 SCH.sub.2 CH.sub.3                                   CH.sub.3        CH.sub.2 SCN(CH.sub.3).sub.2                                  CH.sub.3        CH.sub.2 SCH.sub.2 (CH.sub.2).sub.3 CH.sub.3                  CH.sub.3        NHCH.sub.3                                                    CH.sub.3        NHCH.sub.2 CH.sub.3                                           CH.sub.3        NH(CH.sub.2).sub.2 CH.sub.3                                   CH.sub.3        NHCH(CH.sub.3).sub.2                                          CH.sub.3        NHCH.sub.2 OCH.sub.3                                          CH.sub.3        NH(CH.sub.2).sub.2 OCH.sub.3                                  CH.sub.3        NH(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3                         CH.sub.3        NHCH.sub.2 CF.sub.3                                           CH.sub.3        NHCH(CH.sub.3)CH.sub.2 OCH.sub.3                              CH.sub.3        N(OH)H                                                        CH.sub.3        N(OH)CH.sub.3                                                 CH.sub.3        N(OH)CH.sub.2 CH.sub.3                                        CH.sub.3        N(OH)CH(CH.sub.3).sub.2                                       CH.sub.3        N(OH)(CH.sub.2).sub.2 CH.sub.3                                CH.sub.3        N(OH)CH.sub.2 CF.sub.3                                        ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                         ##STR26##                                                                    Formula 4                                                                     R.sub.4         R.sub.2                                                       ______________________________________                                        CH.sub.3        CH.sub.2 CN                                                   CH.sub.3        CH(CH.sub.3)CN                                                CH.sub.3        CH.sub.2 SCN                                                  CH.sub.3        CH(CH.sub.3)SCN                                               CH.sub.3        CH.sub.2 NH.sub.2                                             CH.sub.3        CH.sub.2 NHCH.sub.3                                           CH.sub.3        CH.sub.2 N(CH.sub.3).sub.2                                    CH.sub.3        CH.sub.2 NHCOCH.sub.3                                         CH.sub.3        CH(CH.sub.3)NHCOCH.sub.3                                      CH.sub.3        CH.sub.2 OH                                                   CH.sub.3        CH(CH.sub.3)OH                                                CH.sub.3        CH.sub.2 OCH.sub.3                                            CH.sub.3        CH.sub.2 OCH.sub.2 CH.sub.3                                   CH.sub.3        CH.sub.2 O(CH.sub.2).sub.2 CH.sub.3                           CH.sub.3        CH.sub.2 O(CH.sub.2).sub.3 CH.sub.3                           CH.sub.3        CH.sub.2 O(CH.sub.2).sub.4 CH.sub.3                           CH.sub.2 CH.sub.3                                                                             CH.sub.2 OCH.sub.2 (CH.sub.2).sub.3 CH.sub.3                  CH.sub.3        CH.sub.2 OCH.sub.2 (CH.sub.2).sub.4 CH.sub.3                  CH.sub.3        CH.sub.2 SCH.sub.3                                            CH.sub.3        CH.sub. 2 SCH.sub.2 CH.sub.3                                  CH.sub.3        CH.sub.2 SCH(CH.sub.3).sub.2                                  CH.sub.3        CH.sub.2 SCH.sub.2 (CH.sub.2).sub.3 CH.sub.3                  CH.sub.3        NHCH.sub.3                                                    CH.sub.3        NHCH.sub.2 CH.sub.3                                           CH.sub.3        NH(CH.sub.2).sub.2 CH.sub.3                                   CH.sub.3        NHCH(CH.sub.3).sub.2                                          CH.sub.3        NHCH.sub.2 OCH.sub.3                                          CH.sub.3        NH(CH.sub.2).sub.2 OCH.sub.3                                  CH.sub.3        NH(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3                         CH.sub.3        NHCH.sub.2 CF.sub.3                                           CH.sub.3        NHCH(CH.sub.3)CH.sub.2 OCH.sub.3                              CH.sub.3        N(OH)H                                                        CH.sub.3        N(OH)CH.sub.3                                                 CH.sub.3        N(OH)CH.sub.2 CH.sub.3                                        CH.sub.3        N(OH)CH(CH.sub.2).sub.2 CH.sub.3                              CH.sub.3        N(OH)(CH.sub.2).sub.2 CH.sub.3                                CH.sub.3        N(OH)CH.sub.2 CF.sub.3                                        ______________________________________                                    

                  TABLE 5                                                         ______________________________________                                         ##STR27##                                                                    Formula 5                                                                     R.sub.4         R.sub.2                                                       ______________________________________                                        CH.sub.3        CH.sub.2 CN                                                   CH.sub.3        CH(CH.sub.3)CN                                                CH.sub.3        CH.sub.2 SCN                                                  CH.sub.3        CH(CH.sub.3)SCN                                               CH.sub.3        CH.sub.2 NH.sub.2                                             CH.sub.3        CH.sub.2 NHCH.sub.3                                           CH.sub.3        CH.sub.2 N(CH.sub.3).sub.2                                    CH.sub.3        CH.sub.2 NHCOCH.sub.3                                         CH.sub.3        CH(CH.sub.3)NHCOCH.sub.3                                      CH.sub.3        CH.sub.2 OH                                                   CH.sub.3        CH(CH.sub.3)OH                                                CH.sub.3        CH.sub.2 OCH.sub.3                                            CH.sub.3        CH.sub.2 OCH.sub.2 CH.sub.3                                   CH.sub.3        CH.sub.2 O(CH.sub.2).sub.2 CH.sub.3                           CH.sub.3        CH.sub.2 O(CH.sub.2).sub.3 CH.sub.3                           CH.sub.3        CH.sub.2 O(CH.sub.2).sub.4 CH.sub.3                           CH.sub.2 CH.sub.3                                                                             CH.sub.2 OCH.sub.2 (CH.sub.2).sub.3 CH.sub.3                  CH.sub.3        CH.sub.2 OCH.sub.2 (CH.sub.2).sub.4 CH.sub.3                  CH.sub.3        CH.sub.2 SCH.sub.3                                            CH.sub.3        CH.sub.2 SCH.sub.2 CH.sub.3                                   CH.sub.3        CH.sub.2 SCH(CH.sub.3).sub.2                                  CH.sub.3        CH.sub.2 SCH.sub.2 (CH.sub.2).sub.3                           CH.sub.3        NHCH.sub.3                                                    CH.sub.3        NHCH.sub.2 CH.sub.3                                           CH.sub.3        NH(CH.sub.2).sub.2 CH.sub.3                                   CH.sub.3        NHCH(CH.sub.3).sub.2                                          CH.sub.3        NHCH.sub.2 OCH.sub.3                                          CH.sub.3        NH(CH.sub.2).sub.2 OCH.sub.3                                  CH.sub.3        NH(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3                         CH.sub.3        NHCH.sub.2 CF.sub.3                                           CH.sub.3        NHCH(CH.sub.3)CH.sub.2 OCH.sub.3                              CH.sub.3        N(OH)H                                                        CH.sub.3        N(OH)CH.sub.3                                                 CH.sub.3        N(OH)CH.sub.2 CH.sub.3                                        CH.sub.3        N(OH)CH(CH.sub.3).sub.2                                       CH.sub.3        N(OH)(CH.sub.2).sub.2 CH.sub.3                                CH.sub.3        N(OH)CH.sub.2 CF.sub.3                                        ______________________________________                                    

                  TABLE 6                                                         ______________________________________                                         ##STR28##                                                                    Formula 6                                                                     R.sub.4         R.sub.2                                                       ______________________________________                                        CH.sub.3        CH.sub.2 CN                                                   CH.sub.3        CH(CH.sub.3)CN                                                CH.sub.3        CH.sub.2 SCN                                                  CH.sub.3        CH(CH.sub.3)SCN                                               CH.sub.3        CH.sub.2 NH.sub.2                                             CH.sub.3        CH.sub.2 NHCH.sub.3                                           CH.sub.3        CH.sub.2 N(CH.sub.3).sub.2                                    CH.sub.3        CH.sub.2 NHCOCH.sub.3                                         CH.sub.3        CH(CH.sub.3)NHCOCH.sub.3                                      CH.sub.3        CH.sub.2 OH                                                   CH.sub.3        CH(CH.sub.3)OH                                                CH.sub.3        CH.sub.2 OCH.sub.3                                            CH.sub.3        CH.sub.2 OCH.sub.2 CH.sub.3                                   CH.sub.3        CH.sub.2 O(CH.sub.2).sub.2 CH.sub.3                           CH.sub.3        CH.sub.2 O(CH.sub.2).sub.3 CH.sub.3                           CH.sub.3        CH.sub.2 O(CH.sub.2).sub.4 CH.sub.3                           CH.sub.2 CH.sub.3                                                                             CH.sub.2 OCH.sub.2 (CH.sub.2).sub.3 CH.sub.3                  CH.sub.3        CH.sub.2 OCH.sub.2 (CH.sub.2).sub.4 CH.sub. 3                 CH.sub.3        CH.sub.2 SCH.sub.3                                            CH.sub.3        CH.sub.2 SCH.sub.2 CH.sub.3                                   CH.sub.3        CH.sub.2 SCH(CH.sub.3).sub.2                                  CH.sub.3        CH.sub.2 SCH.sub.2 (CH.sub.2).sub.3                           CH.sub.3        NHCH.sub.3                                                    CH.sub.3        NHCH.sub.2 CH.sub.3                                           CH.sub.3        NH(CH.sub.2).sub.2 CH.sub.3                                   CH.sub.3        NHCH(CH.sub.3).sub.2                                          CH.sub.3        NHCH.sub.2 OCH.sub.3                                          CH.sub.3        NH(CH.sub.2).sub.2 OCH.sub.3                                  CH.sub.3        NH(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3                         CH.sub.3        NHCH.sub.2 CF.sub.3                                           CH.sub.3        NHCH(CH.sub.3)CH.sub.2 OCH.sub.3                              CH.sub.3        N(OH)H                                                        CH.sub.3        N(OH)CH.sub.3                                                 CH.sub.3        N(OH)CH.sub.2 CH.sub.3                                        CH.sub.3        N(OH)CH(CH.sub.3).sub.2                                       CH.sub.3        N(OH)(CH.sub.2).sub.2 CH.sub.3                                CH.sub.3        N(OH)CH.sub.2 CF.sub.3                                        ______________________________________                                    

                  TABLE 7                                                         ______________________________________                                         ##STR29##                                                                    Formula 7                                                                     R.sub.4        R.sub.2                                                        ______________________________________                                        CH.sub.3       CH.sub.2 CN                                                    CH.sub.3       CH(CH.sub.3)CN                                                 CH.sub.3       CH.sub.2 SCN                                                   CH.sub.3       CH(CH.sub.3)SCN                                                CH.sub.3       CH.sub.2 NH.sub.2                                              CH.sub.3       CH.sub.2 NHCH.sub.3                                            CH.sub.3       CH.sub.2 N(CH.sub.3).sub.2                                     CH.sub.3       CH.sub.2 NHCOCH.sub.3                                          CH.sub.3       CH(CH.sub.3)NHCOCH.sub.3                                       CH.sub.3       CH.sub.2 OH                                                    CH.sub.3       CH(CH.sub.3)OH                                                 CH.sub.3       CH.sub.2 OCH.sub.3                                             CH.sub.3       CH.sub.2 OCH.sub.2 CH.sub.3                                    CH.sub.3       CH.sub.2 O(CH.sub.2).sub.2 CH.sub.3                            CH.sub.3       CH.sub.2 O(CH.sub.2).sub.3 CH.sub.3                            CH.sub.3       CH.sub.2 O(CH.sub.2).sub.4 CH.sub.3                            CH.sub.3       CH.sub.2 OCH.sub.2 (CH.sub.2).sub.4 CH.sub.3                   CH.sub.3       CH.sub.2 SCH.sub.3                                             CH.sub.3       CH.sub.2 SCH.sub.2 CH.sub. 3                                   CH.sub.3       CH.sub.2 SCH(CH.sub.3).sub.2                                   CH.sub.3       CH.sub.2 SCH.sub.2 (CH.sub.2).sub.3                            CH.sub.3       NHCH.sub.3                                                     CH.sub.3       NHCH.sub.2 CH.sub.3                                            CH.sub.3       NH(CH.sub.2).sub.2 CH.sub.3                                    CH.sub.3       NHCH(CH.sub.3).sub.2                                           CH.sub.3       NHCH.sub.2 OCH.sub.3                                           CH.sub.3       NH(CH.sub.2).sub.2 OCH.sub.3                                   CH.sub.3       NH(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3                          CH.sub.3       NHCH.sub.2 CF.sub.3                                            CH.sub.3       NHCH(CH.sub.3)CH.sub.2 OCH.sub.3                               CH.sub.3       N(OH)H                                                         CH.sub.3       N(OH)CH.sub.3                                                  CH.sub.3       N(OH)CH.sub.2 CH.sub.3                                         CH.sub.3       N(OH)CH(CH.sub.3).sub.2                                        CH.sub.3       N(OH)(CH.sub.2).sub.2 CH.sub.3                                 CH.sub.3       N(OH)CH.sub.2 CF.sub.3                                         ______________________________________                                    

                  TABLE 8                                                         ______________________________________                                         ##STR30##                                                                    Formula 8                                                                     R.sub.1           R.sub.13    R.sub.3                                         ______________________________________                                        NO.sub.2          OH          OCH.sub.3                                       C(CH.sub.3)(NOCH.sub.3)                                                                         OH          Cl                                              CO.sub.2 CH.sub.3 OH          Cl                                              COCH.sub.2 CH.sub.3                                                                             OH          Cl                                              C(CH.sub.3)(OCH.sub.3).sub.2                                                                    OH          Cl                                              CH(OCH.sub.3).sub.2                                                                             OH          Cl                                              CH(OCH.sub.2 CH.sub.2 O)                                                                        OH          Cl                                              SO.sub.2 CH.sub.2 CH.sub.3                                                                      OH          OCH.sub.3                                       NO.sub.2          OH          CH.sub.3                                        NO.sub.2          OCH.sub.3   OCH.sub.3                                       C(CH.sub.3)(NOCH.sub.3)                                                                         OCH.sub.3   Cl                                              CO.sub.2 CH.sub.3 OCH.sub.3   Cl                                              COCH.sub.2 CH.sub.3                                                                             OCH.sub.3   Cl                                              C(CH.sub.3)(OCH.sub.3).sub.2                                                                    OCH.sub.3   Cl                                              CH(OCH.sub.3).sub.2                                                                             OCH.sub.3   Cl                                              CH(OCH.sub.2 CH.sub.2 O)                                                                        OCH.sub.3   Cl                                              SO.sub.2 CH.sub.2 CH.sub.3                                                                      OCH.sub.3   CH.sub.3                                        NO.sub.2          OCH.sub.3   Cl                                              ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                         ##STR31##                                                                    Formula 9                                                                     R.sub.1           R.sub.13    R.sub.3                                         ______________________________________                                        NO.sub.2          OH          OCH.sub.3                                       C(CH.sub.3)(NOCH.sub.3)                                                                         OH          Cl                                              CO.sub.2 CH.sub.3 OH          Cl                                              COCH.sub.2 CH.sub.3                                                                             OH          Cl                                              C(CH.sub.3)(OCH.sub.3).sub.2                                                                    OH          Cl                                              CH(OCH.sub.3).sub.2                                                                             OH          Cl                                              CH(OCH.sub.2 CH.sub.2 O).sub.2                                                                  OH          Cl                                              SO.sub.2 CH.sub.2 CH.sub.3                                                                      OH          Cl                                              NO.sub.2          OH          CH.sub.3                                        NO.sub.2          OCH.sub.3   OCH.sub.3                                       C(CH.sub.3)(NOCH.sub.3)                                                                         OCH.sub.3   Cl                                              CO.sub.2 CH.sub.3 OCH.sub.3   Cl                                              COCH.sub.2 CH.sub.3                                                                             OCH.sub.3   Cl                                              C(CH.sub.3)(OCH.sub.3).sub.2                                                                    OCH.sub.3   Cl                                              CH(OCH.sub.3).sub.2                                                                             OCH.sub.3   Cl                                              CH(OCH.sub.2 CH.sub.2 O).sub.2                                                                  OCH.sub.3   Cl                                              SO.sub.2 CH.sub.2 CH.sub.3                                                                      OCH.sub. 3  CH.sub.3                                        NO.sub.2          OCH.sub.3   CH.sub.3                                        ______________________________________                                    

                  TABLE 10                                                        ______________________________________                                         ##STR32##                                                                    Formula 10                                                                    R.sub.1           R.sub.13    R.sub.3                                         ______________________________________                                        NO.sub.2          OH          OCH.sub.3                                       C(CH.sub.3)(NOCH.sub.3)                                                                         OH          Cl                                              CO.sub.2 CH.sub.3 OH          Cl                                              COCH.sub.2 CH.sub.3                                                                             OH          Cl                                              C(CH.sub.3)(OCH.sub.3).sub.2                                                                    OH          Cl                                              CH(OCH.sub.3).sub.2                                                                             OH          Cl                                              CH(OCH.sub.2 CH.sub.2 O).sub.2                                                                  OH          Cl                                              SO.sub.2 CH.sub.2 CH.sub.3                                                                      OH          CH.sub.3                                        NO.sub.2          OH          CH.sub.3                                        C(CH.sub.3)(NOCH.sub.3)                                                                         OCH.sub.3   Cl                                              CO.sub.2 CH.sub.3 OCH.sub.3   Cl                                              COCH.sub.2 CH.sub.3                                                                             OCH.sub.3   Cl                                              C(CH.sub.3)(OCH.sub.3).sub.2                                                                    OCH.sub.3   Cl                                              CH(OCH.sub.3).sub.2                                                                             OCH.sub.3   Cl                                              CH(OCH.sub.2 CH.sub.2 O).sub.2                                                                  OCH.sub.3   Cl                                              ______________________________________                                    

                  TABLE 11                                                        ______________________________________                                         ##STR33##                                                                     Formula 11                                                                   R         X           Y            Z                                          ______________________________________                                        H         CH.sub.2 CH.sub.3                                                                         OCH.sub.3    CH                                         H         CH.sub.2 CH.sub.3                                                                         OCH.sub.2 CH.sub.3                                                                         CH                                         H         OCH.sub.2 CH.sub.3                                                                        OCH.sub.2 CH.sub.3                                                                         CH                                         CH.sub.3  OCH.sub.3   NHCH.sub.3   N                                          CH.sub.3  CH.sub.3    NHCH.sub.3   N                                          ______________________________________                                    

                  TABLE 12                                                        ______________________________________                                         ##STR34##                                                                    Formula 12                                                                    R.sub.4          R.sub.2                                                      ______________________________________                                        CH.sub.3         CH.sub.2 CN                                                  CH.sub.3         CH(CH.sub.3)CN                                               CH.sub.3         CH.sub.2 SCN                                                 CH.sub.3         CH(CH.sub.3)SCN                                              CH.sub.3         CH.sub.2 NH.sub.2                                            CH.sub.3         CH.sub.2 NHCH.sub.3                                          CH.sub.3         CH.sub.2 N(CH.sub.3).sub.2                                   CH.sub.3         CH.sub.2 NHCOCH.sub.3                                        CH.sub.3         CH(CH.sub.3)NHCOCH.sub.3                                     CH.sub.3         CH.sub.2 OH                                                  CH.sub.3         CH(CH.sub.3)OH                                               CH.sub.3         CH.sub.2 OCH.sub.3                                           CH.sub.3         CH.sub.2 OCH.sub.2 CH.sub.3                                  CH.sub.3         CH.sub.2 O(CH.sub.2).sub.2 CH.sub.3                          CH.sub.3         CH.sub.2 O(CH.sub.2).sub.3 CH.sub.3                          CH.sub.3         CH.sub.2 O(CH.sub.2).sub.4 CH.sub.3                          CH.sub.2 CH.sub.3                                                                              CH.sub.2 OCH.sub.2 (CH.sub.2).sub.3 CH.sub.3                 CH.sub.3         CH.sub.2 OCH.sub.2 (CH.sub.2).sub.4 CH.sub.3                 CH.sub.3         CH.sub. 2 SCH.sub.3                                          CH.sub.3         CH.sub.2 SCH.sub.2 CH.sub.3                                  CH.sub.3         N(OH)H                                                       CH.sub.3         N(OH)CH.sub.3                                                CH.sub.3         N(OH)CH.sub.2 CH.sub.3                                       CH.sub.3         N(OH)CH(CH.sub.3).sub.2                                      CH.sub.3         N(OH)(CH.sub.2).sub.2 CH.sub.3                               CH.sub.3         N(OH)CH.sub.2 CF.sub.3                                       ______________________________________                                    

                  TABLE 13                                                        ______________________________________                                         ##STR35##                                                                    Formula 13                                                                    R.sub.4         R.sub.2                                                       ______________________________________                                        CH.sub.3        CH.sub.2 CN                                                   CH.sub.3        CH(CH.sub.3)CN                                                CH.sub.3        CH.sub.2 SCN                                                  CH.sub.3        CH(CH.sub.3)SCN                                               CH.sub.3        CH.sub.2 NH.sub.2                                             CH.sub.3        CH.sub.2 NHCH.sub.3                                           CH.sub.3        CH.sub.2 N(CH.sub.3).sub.2                                    CH.sub.3        CH.sub.2 NHCOCH.sub.3                                         CH.sub.3        CH(CH.sub.3)NHCOCH.sub.3                                      CH.sub.3        CH.sub.2 OH                                                   CH.sub.3        CH(CH.sub.3)OH                                                CH.sub.3        CH.sub.2 OCH.sub.3                                            CH.sub.3        CH.sub.2 OCH.sub.2 CH.sub.3                                   CH.sub.3        CH.sub.2 O(CH.sub.2).sub.2 CH.sub.3                           CH.sub.3        CH.sub.2 O(CH.sub.2).sub.3 CH.sub.3                           CH.sub.3        CH.sub.2 O(CH.sub.2).sub.4 CH.sub.3                           CH.sub.3        CH.sub.2 OCH.sub.2 (CH.sub.2).sub.4 CH.sub.3                  CH.sub.3        CH.sub.2 SCH.sub.3                                            CH.sub.3        CH.sub.2 SCH.sub.2 CH.sub.3                                   CH.sub.3        N(OH)H                                                        CH.sub.3        N(OH)CH.sub.3                                                 CH.sub.3        N(OH)CH.sub.2 CH.sub.3                                        CH.sub.3        N(OH)CH(CH.sub.3).sub.2                                       CH.sub.3        N(OH)(CH.sub.2).sub.2 CH.sub.3                                CH.sub.3        N(OH)CH.sub.2 CF.sub.3                                        ______________________________________                                    

Formulations

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectare. High strengthcompositions are primarily used as intermediates for furtherformulations. The formulations, broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid and/or liquid diluent(s).More specifically, they will contain these ingredients in the followingapproximate proportions:

    ______________________________________                                                    Weight Percent*                                                               Active                                                                        Ingredient                                                                            Diluent(s)                                                                              Surfactant(s)                                   ______________________________________                                        Wettable Powders                                                                            20-90      0-74     1-10                                        Oil Suspensions,                                                                             3-50     40-95     0-15                                        Emulsions, Solutions,                                                         (including Emulsifiable                                                       Concentrates)                                                                 Aqueous Suspension                                                                          10-50     40-84     1-20                                        Dusts          1-25     70-99     0-5                                         Granules and Pellets                                                                        0.1-95      5-99.9  0-15                                        High Strength 90-99      0-10     0-2                                         Compositions                                                                  ______________________________________                                         *Active ingredient plus at least one of a Surfactant or Diluent equals 10     weight percent.                                                          

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, N.J., but other solids, either mined or manufactured, may beused. The more absorptive diluents are preferred for wettable powdersand the denser ones for dusts. Typical liquid diluents and solvents aredescribed in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York,1950. Solubility under 0.1% is preferred for suspension concentrates;solution concentrates are preferably stable against phase separation at0° C. "McCutcheon's Detergents and Emulsifiers Annual:, MC PublishingCorp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia ofSurface Active Agents", Chemical Publishing Co., Inc., New York, 1964,list surfactants and recommended uses. All formulations can containminor amounts of additives to reduce foaming, caking corrosion,microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook", 5th Ed., McGraw-Hill, New York, 1973, 8-57ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16through Col. 7, line 19 and Examples 10 through 41.

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, Jun. 23, 1959, Col. 3,line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc.,New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwiseindicated.

EXAMPLE 9

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        Methyl 2-[[[[(4,6-dimethoxypyrimidin-2-yl)amino]-                                                       80%                                                 carbonyl]amino]sulfonyl]-5-(methoxyethyl)-                                    benzoate                                                                      sodium alkylnaphthalenesulfonate                                                                        2%                                                  sodium ligninsulfonate    2%                                                  synthetic amorphous silica                                                                              3%                                                  kaolinite                 13%                                                 ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids areessentially under 50 microns, reblended, and packaged.

EXAMPLE 10

    ______________________________________                                        Methyl 2-[[[[(4,6-dimethoxypyrimidin-2-yl)amino]-                                                       50%                                                 carbonyl]amino]sulfonyl]-5-(hydroxymethyl)-                                   benzoate                                                                      sodium alkylnaphthalenesulfonate                                                                         2%                                                 low viscosity methyl cellulose                                                                           2%                                                 diatomaceous earth        46%                                                 ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milledto produce particles essentially all below 10 microns in diameter. Theproduct is reblended before packaging.

EXAMPLE 11

    ______________________________________                                        Granule                                                                       ______________________________________                                        Wettable Powder of Example 10                                                                         5%                                                    attapulgite granules   95%                                                    (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                             ______________________________________                                    

A slurry of wettable powder containing 25% solids is sprayed on thesurface of attapulgite granules in a double-cone blender. The granulesare dried and packed.

EXAMPLE 12

    ______________________________________                                        Extruded Pellet                                                               ______________________________________                                        Methyl 2-[[[[(4,6-dimethoxypyrimidin-2-yl)amino]-                                                         25%                                               carbonyl]amino]sulfonyl]-5-(methoxymethyl)-                                   benzoate                                                                      anhydrous sodium sulfate    10%                                               crude calcium ligninsulfonate                                                                              5%                                               sodium alkylnaphthalenesulfonate                                                                           1%                                               calcium/magnesium bentonite 59%                                               ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

EXAMPLE 13

    ______________________________________                                        Methyl 2-[[[[(4,6-dimethoxypyrimidin-2-yl)amino]-                                                         1%                                                carbonyl]amino]sulfonyl]-5-(hydroxymethyl)-                                   benzoate                                                                      N,N-dimethylformamide       9%                                                attapulgite granules        90%                                               (U.S.S. 20 to 40 sieve)                                                       ______________________________________                                    

The active ingredient is dissolved is dissolved in the solvent and thesolution is sprayed upon dedusted granules in a double-cone blender.After spraying of the solution has been completed, the blender isallowed to run for a short period and then the granules are packaged.

EXAMPLE 14

    ______________________________________                                        Methyl 2-[[[[(4,6-dimethoxypyrimidin-2-yl)amino]-                                                         80%                                               carbonyl]amino]sulfonyl]-5-(methoxymethyl)-                                   benzoate                                                                      wetting agent                1%                                               crude ligninsulfonate salt  20%                                               (containing 5-20% of the natural                                              sugars)                                                                       attapulgite clay             9%                                               ______________________________________                                    

The ingredients are blended and milled to pass through a 100 meshscreen. This material is then added to a fluid bed granulator, the airflow is adjusted to gently fluidize the material, and a fine spray ofwater is sprayed onto the fluidized material. The fluidization andspraying are continued until granules of the desired size range aremade. The spraying is stopped, but fluidization is continued, optionallywith heat, until the water content is reduced to the desired level,generally less than 1%. The material is then discharged, screened to thedesired size range, generally 14-100 mesh (1410-149 microns), andpackaged for use.

EXAMPLE 15

    ______________________________________                                        Methyl 2-[[[[(4,6-dimethoxypyrimidin-2-yl)amino]-                                                       1%                                                  carbonyl]amino]sulfonyl]-5-(hydroxymethyl)-                                   benzoate                                                                      N,N-dimethylformamide     9%                                                  attapulgite granules      90%                                                 (U.S.S. 20 to 40 sieve)                                                       ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution issprayed upon dedusted granules in a double cone blender. After sprayingof the solution has been completed, the blender is allowed to run for ashort period and then the granules are packaged.

EXAMPLE 16

    ______________________________________                                        Methyl 2-[[[[(4,6-dimethoxypyrimidin-2-yl)amino]-                                                         40%                                               carbonyl]amino]sulfonyl]-5-(methoxymethyl)-                                   benzoate                                                                      polyacrylic acid thickener  0.3%                                              dodecylphenol polyethylene glycol                                                                         0.5%                                              ether                                                                         disodium phosphate          1%                                                monosodium phosphate        0.5%                                              polyvinyl alcohol           1.0%                                              water                       56.7%                                             ______________________________________                                    

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 17

    ______________________________________                                        Solution                                                                      ______________________________________                                        Methyl 2-[[[[(4,6-dimethoxypyrimidin-2-yl)amino]-                                                          5%                                               carbonyl]amino]sulfonyl]-5-(hydroxymethyl)-                                   benzoate                                                                      water                       95%                                               ______________________________________                                    

The salt is added directly to the water with stirring to produce thesolution, which may then be packaged for use.

EXAMPLE 18

    ______________________________________                                        High Strength Concentrate                                                     ______________________________________                                        Methyl 2-[[[[(4,6-dimethoxypyrimidin-2-yl)amino]-                                                         99%                                               carbonyl]amino]sulfonyl]-5-(methoxymethyl)-                                   benzoate                                                                      silica aerogel              0.5%                                              synthetic amorphous silica  0.5%                                              ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce amaterial essentially all passing a U.S.S. No. 50 screen (0.3 mmopening). The concentrate may be formulated further if necessary.

EXAMPLE 19

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        Methyl 2-[[[[(4,6-dimethoxypyrimidin-2-yl)amino]-                                                         90%                                               carbonyl]amino]sulfonyl]-5-(hydroxymethyl)-                                   benzoate                                                                      dioctyl sodium sulfosuccinate                                                                             0.1%                                              synthetic fine silica       9.9%                                              ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produceparticles essentially all below 100 microns. The material is siftedthrough a U.S.S. No. 50 screen and then packaged.

EXAMPLE 20

    ______________________________________                                        Methyl 2-[[[[(4,6-dimethoxypyrimidin-2-yl)amino]-                                                         40%                                               carbonyl]amino]sulfonyl]-5-(methoxymethyl)-                                   benzoate                                                                      sodium ligninsulfonate      20%                                               montmorillonite clay        40%                                               ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and thenair-milled to produce particles essentially all below 10 microns insize. The material is reblended and then packaged.

EXAMPLE 21

    ______________________________________                                        Methyl 2-[[[[(4,6-dimethoxypyrimidin-2-yl)amino]-                                                         35%                                               carbonyl]amino]sulfonyl]-5-(hydroxymethyl)-                                   benzoate                                                                      blend of polyalcohol carboxylic                                                                            6%                                               esters and oil soluble petroleum                                              sulfonates                                                                    xylene                      59%                                               ______________________________________                                    

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 5 microns. The product can beused directly, extended with oils, or emulsified in water.

EXAMPLE 22

    ______________________________________                                        Methyl 2-[[[[(4,6-dimethoxypyrimidin-2-yl)amino]-                                                         10%                                               carbonyl]amino]sulfonyl]-5-(methoxymethyl)-                                   benzoate                                                                      attapulgite                 10%                                               Pyrophyllite                80%                                               ______________________________________                                    

The active ingredient is blended with attapulgite and then passedthrough a hammer-mill to produce particles substantially all below 200microns. The ground concentrate is then blended with powderedpyrophyllite until homogeneous.

EXAMPLE 23

    ______________________________________                                        Methyl 2-[[[[(4,6-dimethoxypyrimidin-2-yl)amino]-                                                         25%                                               carbonyl]amino]sulfonyl]-5-(hydroxymethyl)-                                   benzoate                                                                      polyoxyethylene sorbitol hexaoleate                                                                        5%                                               highly aliphatic hydrocarbon oil                                                                          70%                                               ______________________________________                                    

The ingredients are ground together in a sand mill until the solidparticles have been reduced to under about 5 microns. The resultingthick suspension may be applied directly, but preferably after beingextended with oils or emulsified in water.

Utility

Many compounds of this invention are particularly useful for the controlof weeds in sugar beets and fodder beets. This is a crop that takes along period to become established. In this interval, the crop seedlingsmust be nurtured carefully, with particular attention to weed control toprevent damage due to competition. The subject compound can be usedeither pre- or post-emergence and will control numerous problem weedsincluding galium (Galium aparine), pigweed (Amaranthus spp.),lambsquarters (Chenopodium album), wild oats (Avena fatua), wild radish(Raphanus raphanistrum), and blackgrass (Alopecurus myosuroides). Someof the compounds of the invention are useful for selective weed controlin other crops such as soybeans. Additionally, some of these compoundsare useful as plant growth regulants or as citrus abscission agents.

The rate of application of a compound from this invention is determinedby a number of factors including the weeds to be controlled, weather andclimate, soil type, time of application, age and size of crop and weeds,method of application (pre- or post-), etc. In general terms, the ratewill vary between about 1 and 20000 g/ha, with a preferred rate of about4 to 500 g/ha. The rate to be used in any given situation can beselected by one with ordinary skill in the art.

These compounds can and will often be used in mixtures with one or moreother herbicides. They may be mixed with any other herbicides selectiveon beets including metamitron, phenmedipham, chloridazin, desmedipham,lenacil, ethofumesate, cycloate, diclorp-methyl, fluazifop, haloxyfop,and quinoxyfop ethyl. Or if used in soybeans, they may be advantageouslymixed with compounds selective on soybeans. These compounds include, butare not restricted to: acifluorfen, alachlor, bentazon, chlorbromuron,chlorimuron ethyl, chloroxuron, diclofop, fexoxaprop ethyl, imazaquin,linuron, metachlor, metribuzin, oxyfluorfen, propachlor, quinoxyfopethyl, sethoxydim, trifluralin, vernolate, 2,4-DB, cinmethylin,imazethapyr, thiameturon methyl, haloxyfop-methyl and2-(2'-chlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone.

Herbicidal properties of compounds of this invention were discovered ina number of greenhouse tests. Test descriptions and results follow.##STR36##

TEST A

Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloacrus-galli), cheatgrass (Bromus secalinus), cocklebur (Xanthiumpensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass(Digitaria spp.), giant foxtail (Setaria faberi), morningglory (Ipomoeaspp.), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycinemax), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti),wheat (Triticum aestivum), and wild oat (Avena fatua) and purplenutsedge (Cyperus rotundus) tubers were planted and treated preemergencewith test chemicals dissolved in a non-phytotoxic solvent. At the sametime, these crop and weed species were also treated with postemergenceapplications of test chemicals. Plants ranged in height from two toeighteen cm (two to three leaf stage) for postemergence treatments.Treated plants and controls were maintained in a greenhouse forapproximately sixteen days, after which all species were compared tocontrols and visually evaluated. The ratings, summarized in Table A, arebased on a scale of 0 to 10 where 0 is no effect and 10 is completecontrol. A dash (-) response means no test result. The accompanyingdescriptive symbols have the following meanings:

C=chlorosis/necrosis;

E=inhibition of emergence;

G=growth retardation;

H=formative effect; and

U=unusual pigmentation.

    TABLE A      POSTEMERGENCE Cmpd 1 Cmpd 2 Cmpd 3 Cmpd 4 Cmpd 5 Cmpd 6 Cmpd 7 Cmpd 9     Cmpd 10 Cmpd 11 Cmpd 12 RATE (g/ha) 50 10 50 10 50 10 50 10 50 10 50 10     50 10 50 10 50 10 50 10 50 10       Barley 9G 6G 8G 0 3C,9G 9G 8G 3C,9G 9G 2C,7G 2C,8G 2C,5G 2C,9G 3C,7G     3C,5G 4G 0 0 9G 2C,7G 9G 3C,8G Barnyardgrass 3C,8H 4G 3C,9H 0 5C,9G 9G     3C,9H 3C,7H 4C,9H 3C,8H 3C,5H 1H 9G 3C,9H 3C,7G 3H 3G 0 3C,7G 3G 2C,5G 0     Cheatgrass 5C,9G 7G 9G 3G 9G 5G 9G 6G 5G 2G 5G 0 0 0 0 0 0 0 2C,4G 0 0 0     Cocklebur 2C,6G 1C 2C,3H 0 10C 10C 4C,9G 2C,8G 9C 3C,8H 2C,2H 1C 10C     4C,9G 3C,9G 2C,7G 0 0 2C 0 2C,4H 0 Corn 3C,8G 3C,6H 3C,9G 2C,3G 3U,9G     3C,9G 4C,9G 3C,9G 1C,2H 3C,9G 3C,6G 3C,8H 9G 3C,9G 9H 2C,5G 2G 0 4C,9G     2C,4G 3C,9H 2C,5G Cotton 3C,7H 0 3C,6G 0 9C 4C,9G 2C,9G 2C,8H 9H 3C,8H     3C,7H 0 9C 4C,9H 3C,6H 2C,4H 0 0 0 0 3C,5G 0 Crabgrass 3C,8G 2G 3G 0     3C,7G 3C,6G 2C,6G 2G 5G 0 2G 0 7G 5G 5G 0 0 0 0 0 0 0 Giant foxtail     3C,9G 3G 3G 0 9C 3C,9G 3C,9G 2C,4G 3C,7G 2G 2C,4G 0 4C,9G 3C,7G 3C,4G 0     0 0 1C 0 0 0 Morningglory 4C,8H 2C,2H 4C,8H 0 5C,9G 5C,9G 4C,9G -- 2C,7G     3G 3C,8H 2C,4H 5C,9G 3C,7H 2C,4G 2G 0 0 1C,3H 0 0 2G Nutsedge 5G 4G 0 0     10C 8G 5G 0 4G 0 0 2G -- 3C,8G 0 0 0 0 0 0 0 0 Rice 9C 4C,9G 5C,9G 7G 9C     9C 5C,9G 5C,9G 5C,9G 5C,9G 5C,9G 3C,8G 5C,9G 5C,9G 4C,9G 8G 4C,9G 5G     4C,9G 3C,8G 5C,9G 8G Sorghum 4C,9G 5G 4C,9G 0 3C,9G 2C,6G 3C,8H 5G 3C,8H     2C,4G 3C,6G 0 3C,7G 3C,7G 3C,6G 2G 2G 0 4C,9G 3C,5G 4C,9G 1C,6G Soybean     2C,2G 1C,2G 1C 0 3C,9G 3C,5H 3C,5H 3C,3H 3C,4H 2H 3C,4H 1C 5H 2H 0 0 0 0     0 0 1C,1H 0 Sugar beet 0 0 1C,2G 0 2C,7G 0 3C,7H 2C,5H 2C,3H 0 2C,5G 0 0     0 0 0 0 0 3C,7G 0 4C,7G 0 Velvetleaf 0 0 1C,1H 0 9C 2C,6G 3C,6G 4G 5G 1H     0 0 4C,9G 4C,9G 0 0 0 0 2C,2G 0 1H 0 Wheat 5G 0 4G 0 9G 6G 2C,9G 8G 8G     4G 5G 0 2C,6G 3G 0 0 0 0 3G 0 5G 0 Wild oat 2G 0 0 0 9G 4G 2C,8G 2G 2G 0     0 0 1C 0 0 0 0 0 0 0 0 0       Cmpd 13 Cmpd 14 Cmpd 15 Cmpd 16 Cmpd 17 Cmpd 18 Cmpd 19 Cmpd 20 Cmpd     21 Cmpd 22 Cmpd 23 RATE (g/ha) 50 10 50 10 50 10 50 10 50 10 50 50 10 50 1     0 50 10 50 10 50 10       Barley 9G 3C,8H 2C,5G 2C,3G 9G 3C,7G 3C,5G 2C,7G 3C,9G 2C,7G 3C,9G 9G     2C,9G 4C,8G 3C,7G 2C,9G 3C,7G 9G 3C,7H 0 0 Barnyardgrass 4C,9H 9G 0 0 9H     2C,3G 3C,9H 3C,5H 4C,8G 2C,4G 3C,6G 4C,9H 9H 3C,5H 3G 4C,9H 3C,7G 9H     3C,7H 0 0 Cheatgrass 3G 0 0 0 3G 0 0 0 6G 5G 3G 8G 2C,7G 2G 0 2C,5G 2G     2G 0 0 0 Cocklebur 9C 5C,9G 3C,7H 0 4C,9G 4C,9G 3C,8H 2H 1H 0 2C,5G 10C     5C,9G 3C,7H 0 4C,9G 4C,9H 4C,9G 3C,8H 2H 1H Corn 2C,9G 3C,9G 2C,7G 1C     4C,9G 3C,9G 2C,4G 0 4C,9G 2C,4G 4C,9G 4C,9G 3C,9G 3C,9G 3C,7G 4C,9G     3C,9H 3C,9H 3C,6G 0 0 Cotton 2C,9G 2C,8G 0 0 3C,7G 2G 2G 0 3C,7H 0 4C,8G     5C,9G 3C,9H 3C,8H 2G 4C,8H 3C,7G 4C,9H 2G 3C,7H 3G Crabgrass 0 0 0 0 0 0     0 0 3C,7G 0 0 3C,5G 0 0 0 0 0 2C,4G 0 0 0 Giant foxtail 2C,2G 0 0 0 3G 0     0 0 3C,7G 2G 2G 4C,9G 3C,7G 0 0 3C,6G 2C,2G 3C,5G 2G 0 0 Morningglory     10C 2C,2H 1C 0 2C,5G 1C 2G 0 3C,8H 3C,6G 4C,9G 4C,9H 3C,7G3C,5H 2H 2C,7H     3C,7H 3C,6G 2H 4C,8H 2C,4H Nutsedge 2C,8G 0 0 0 0 0 -- 0 0 0 0 4C,9G     2C,7G -- 0 3C,8G 0 5C,9G 4G 5G 0 Rice 5C,9G 4C,9G 3C,7G 3G 4C,9G 7G     4C,9G 5G 9C 5C,9G 5C,9G 9C 5C,9G 9C 3C,9G 5C,9G 5C,9G 5C,9G 5C,9G 0 0     Sorghum 3C,9G 9G 3C,8G 2G 4C,9G 3C,8G 4C,9G 2G 4C,9G 4C,9G 4C,9G 4C,9G     9G 4C,8G 3C,7G 4C,9H 3C,7G 3C,9G 3C,8G 3C,7G 0 Soybean 3C,8G 3C,7H 0 0     2C,3H 1H 0 0 3C,9H 2C,5H 3C,8H 3C,8H 3C,8G 3C,6H 1H 3C,8H 4H 2H 0 4C,9G     2C,8G Sugar beet 1C 0 1H 0 2H 0 3G 0 10C 5C,9G 5C,9G 9C 4C,7G4C,8G 3C,7G     4C,9H 3C,5H 4C,9G 2G 5C,9G 4C,9G Velvetleaf 4C,8G 6G 0 0 0 0 0 0 0 0     4C,8G 5C,9G 3C,7G7H 1H 3C,7G 0 2C,5G 1H 3G 0 Wheat 5G 3G 0 0 8G 5G 0 0     2C,6G 0 5G 9G 6G2C,8G 2G 9G 6G 4G 0 0 0 Wild oat 0 0 0 0 2C,3G 0 0 0 1C     0 2G 2C,7G 2C,5G1C 0 2C,5G 3C,3G 0 0 0 0       Cmpd 24 Cmpd 25 Cmpd 26 Cmpd 27 Cmpd 28 Cmpd 29 Cmpd 30 Cmpd 31 Cmpd     32 Cmpd 33  Cmpd 34 RATE (g/ha) 50 10 50 10 50 10 50 10 50 10 50 10 50     10 50 10 50 10 50 10 50 10       Barley 0 0 3C,7G 0 0 0 3G 0 0 0 8G 7G 8G 6G 9G 8G 8G 4G 4G 0 0 0     Barnyardgrass 0 0 4C,8H 2C,5G 3C,6G 2G 0 0 2G 0 3C,8H 4H 2C,4H 2H 10C     3C,9H 3C,9H 3H 4C,9H 2C,5H 0 0 Cheatgrass 0 0 2C,5G 0 0 0 0 0 5G 0 5G 0     0 0 4G 0 5G 3G 5G 0 0 0 Cocklebur 2C,2H 1H 4C,9G 4C,9G 3C,6H 3G 2C,5G 0     0 0 3C,6H 3H 2H 0 10C 7C 3C,9H 3C,9H 4C,8H 2C,5H 0 0 Corn 0 0 5U,9G     3C,8G 3C,7G 3G 3C,5H 0 2C,3G 0 3C,9G 2C,6H 3U,9G 3C,6H 10C 4U,9G 3C,9G     8H 2C,3G 1C,2G 2C,5G 0 Cotton 2C,5G 0 3C,8G 2C,7G 3C,7G 2C,3H 7H 0 3C,5G     0 3G 0 5G 0 9G 9G 9G 6G 2G 0 0 0 Crabgrass 0 0 2G 0 0 0 0 0 0 0 4G 0 2G     0 5G 0 2G 0 0 0 0 0 Giant foxtail 0 0 3C,8G 0 3C,5G 0 0 0 0 0 2G 0 0 0     3C,8G 2G 0 0 0 0 3G 0 Morningglory 4C,8G 2C,2H 5C,9G 1C,2H 3C,8H 0 2C,2H     0 0 0 3H 0 4H 0 3C,4H 0 1C,2G 1C,1H 0 0 0 0 Nutsedge 8G 0 -- 3C,6G 0 0 0     0 0 0 0 0 0 0 3C,9G 2C,5G 0 0 0 0 0 0 Rice 3C,7G 1C 9C 3C,8G 4C,8G 5G 9C     0 7G 2G 9C 7G 5C,9G 7G 9C 4C,8G 5C,9G 8G 7G 7G 2C,5G 3G Sorghum 3G 0     3C,9G 3C,7G 3C,8G 0 4G 0 6G 2G 3C,9G 7H 3C,8G 5G 9C 9G 4C,9G 6G 8G 2G 5G     0 Soybean 2C,6H 1C,2H 3C,8G 2H 3C,8G 2C,2H 2H 0 3C,7H 0 1C,1H 1H 1C,1H 0     8G 6H 4H 2H 0 0 0 0 Sugar beet 5C,9G 3C,6H 9C 3C,6G 5C,9G 3G 5G 0 2C,2H     1H 5G -- 0 0 1C 0 2G 0 0 0 4G 0 Velvetleaf 3C,7G 2C 3C,7G 5G 7G 2G 4G 0     7G 0 4G 0 3C,5H 0 4C,9G 8G 4G 0 2G 0 0 0 Wheat 0 0 6G 0 2G 0 0 0 0 0 0 0     0 0 5G 2G 7G 0 0 0 0 0 Wild oat 0 0 2C,2G 0 0 0 0 0 0 0 0 0 0 0 2C,4G 2G     2C,3G 0 0 0 4G 0       PREEMERGENCE Cmpd 1 Cmpd 2 Cmpd 3 Cmpd 4 Cmpd 5 Cmpd 6 Cmpd 7 Cmpd 9     Cmpd 10 Cmpd 11 Cmpd 12 RATE (g/ha) 50 10 50 10 50 10 50 10 50 10 50 10     50 10 50 10 50 10 50 10 50 10       Barley 8G 7G 6G 0 9G 8G 2C,9G 7G 9G 8G 7G 2C,7G 3C,6G 0 2C,2G 0 0 0 8G     0 3C,8G 6G Barnyardgrass 0 0 0 0 9H 2C,4H 3C,7G 1C 8H 2G 0 0 3C,7G 0 0 0     0 0 0 0 1C 0 Cheatgrass 0 0 0 0 6G 2G 8G 5G 7G 4G 4G 0 3G 0 0 0 0 0 5G 0     3G 0 Cocklebur 0 0 4G 2G 9H 8H 3C,6H 2C,2G 3C,6H 2G 0 0 5H 0 0 0 0 0 0 0     1C 0 Corn 2C,4G 0 0 0 9G 8G 3C,7G 2C,2G 3C,9G 2C,6G 3G 0 4C,8H 2C,3G 5G     0 0 0 3C,4G 0 2C 0 Cotton 0 0 2G 0 3C,9G 7G 2C,4H 2G 6G 0 2G 0 7G 0 0 0     0 0 2G 0 0 0 Crabgrass 0 0 2G 0 2C,7G 3G 8G 0 8G 2G -- 0 0 0 0 0 0 0 5G     0 0 0 Giant foxtail 2G 0 3G 0 9G 8G 2C,8G 0 7G 2G 5G 0 2G 0 0 0 0 0 0 0     2C 0 Morningglory 0 0 4G 0 9G 9G 3C,8H 2C,2H 7H 3C,5G 2G 2G 9G 4G 2G 0 0     0 0 0 0 0 Nutsedge 10E 0 0 0 3C,9G 0 5G 3G 7G -- 0 0 0 0 0 0 0 0 0 0 0 0     Rice 7G 0 4G 0 10H 7H 3C,7H 4G 4C,9H 2C,7H 3C,5G 0 9H 3G 7G 0 0 0 8G 0     8G 2G Sorghum 2C,4G 0 2C,5G 0 3C,9H 2C,4G 3C,7G 2C,2G 3C,8H 2C,5G 2C,4G     0 4C,9G 2C,3G 3C,7G 0 0 0 3C,6G 0 3C,7G 2C Soybean 2C,3G 2G 2G 0 4C,8H     2G 3C,4H 2H 2C,7H 2G 6G 3G 2C,2G 0 1C 0 0 0 0 0 0 0 Sugar beet 0 0 0 0 0     0 3C,6H 1H 5G 3G 2G 0 2G 0 3H 0 0 0 2H 0 2H 0 Velvetleaf 0 0 0 0 2C,6G     3G 2C,3H 1H 3H 0 0 3H 2H 2G 0 0 0 0 0 0 0 0 Wheat 6G 0 0 0 9G 6G 8G 6G     8G 4G 3G 0 7G 3G 0 0 0 0 5G 0 5G 2G Wild oat 2G 0 0 0 5G 0 2C,7G 3G 3G 0     2G 0 3G 0 0 0 0 0 2G 0 2G 0       Cmpd 13 Cmpd 14 Cmpd 15 Cmpd 16 Cmpd 17 Cmpd 18 Cmpd 19 Cmpd 20 Cmpd     21 Cmpd 22 Cmpd 23 RATE (g/ha) 50 10 50 10 50 10  50 10 50 10 50 50 10     50 10 50 10 50 10 50 10       Barley 3C,8G 2C,6G 5G 0 2C,8G 5G 3C,8G 3G 2C,7G 2C,5G 2C,7G 8G 6G 7G 0     2C,8G 5G 8G 2C,6G 0 0 Barnyardgrass 3C,9H 2C,3G 0 0 3C,7G 1C 3C,6G 1C 0     0 2G 9H 3C,8H 1C 0 4C,9H 3C,5G 4C,9H 3C,7G 0 0 Cheatgrass 7G 3G 0 0 5G 0     0 0 2G 0 5G 8G 7G 3G 0 8G 5G 5G 3G 0 0 Cocklebur 8H 2C,7H -- 0 2C,5G 2C     3C,3G 0 1C 0 2H 9H 3C,5H 0 0 3C,5H 2C -- 2G 0 2H Corn 3C,9G 3C,6G 2G 0     3C,7G 3C,4G 3C,5G 2C,2G 2C,2G 0 3C,5G 4C,9G 3C,7G 2C,2G 0 4C,9G 3C,5G     3C,8H 3C,3G 2G 0 Cotton 8G 3H 0 0 0 0 2G 0 4G 0 5G 8G 7G 2G 0 3H 0 1H 0     3G 0 Crabgrass 5G 0 0 0 2G 0 0 0 0 0 2G 6G 0 4G 0 5G 0 5G 0 0 0 Giant     foxtail 5G 0 0 0 1C 0 0 0 0 0 0 8G 7G 0 0 3C,5G 0 3C,5G 0 0 0 Morningglor     y 6H 2G 1H 0 2C 0 2G 0 7H 0 2C,5G 5G 5G 1C 0 2C,7G 0 7H 0 3H 2G Nutsedge     3C,5G 0 0 0 0 0 0 0 0 0 0 8G 0 0 0 4G 0 0 0 0 0 Rice 9H 7G 5G 0 2C,7G 2G     5G 2G 8H 0 7G 9H 9H 7G 0 4C,8G 5G 9H 8H 4G 2G Sorghum 9H 3C,6G 1C 0     3C,7G 3C,3G 3C,7G 4G 3C,7G 1C 3C,7G 2C,9G 3C,8H 3C,5G 0 4C,7H 3C,3G     4C,9H 3C,6G 0 0 Soybean 3C,6G 3C,3H 1H 0 2C 0 0 0 5G 3C,3H 4G 3C,7H     3C,5G 2C,2H 0 3C,3H 1C 3C,3H 1C,1H 5G 2C,2H Sugar beet 0 0 3G 0 2G 3H 4H     0 4C,9G 4G 4C,8G 0 0 4H 0 5H 2H 9G 0 6G 4G Velvetleaf 2C,5H 3H 0 0 2C 1C     0 0 0 0 1H 7H 0 1H 0 3H 1H 2G 0 0 0 Wheat 7G 6G 2G 0 7G 3G 2G 0 3G 0 5G     7G 7G 5G 0 8G 5G 6G 2G 0 0 Wild oat 2C,3G 2G 0 0 2G 0 0 0 0 0 1C 3C,6G     2C,3G 2G 0 3C,6G 2C,4G 2C,2G 1C 0 0       Cmpd 24 Cmpd 25 Cmpd 26 Cmpd 27 Cmpd 28 Cmpd 29 Cmpd 30 Cmpd 31 Cmpd     32 Cmpd 33 Cmpd 34 RATE (g/ha) 50 10 50 10 50 10 50 10 50 10 50 10 50 10 5     0 10 50 10 50 10 50 10       Barley 0 0 0 0 0 0 0 0 0 0 8G 0 7G 0 8G 0 7G 0 7G 0 0 0 Barnyardgrass     0 0 0 0 0 0 0 0 0 0 0 0 0 0 3C,9H 2C,6H 3C,6H 0 5H 0 0 0 Cheatgrass 0 0     2G 0 0 0 0 0 0 0 0 0 0 0 6G 2G 2G 0 0 0 0 0 Cocklebur 0 0 2C,4G 0 0 0 2G     0 0 0 2C 0 2H 0 9H 3C,4H 3C,3G 1C 0 0 2G 0 Corn 2G 0 3G 0 2C,2G 0 0 0 0     0 1C 0 3C,6G 0 3C,9G 2C,4G 4C,6G 2C 1C,2G 0 0 0 Cotton 4G 0 4G 0 2G 0 0     0 0 0 0 0 0 0 5G 0 0 0 0 0 0 0 Crabgrass 0 0 3G 0 0 0 0 0 0 0 0 0 0 0     2C,3H 0 0 0 0 0 3G 0 Giant foxtail 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6H 2H 0 0     0 0 0 0 Morningglory 2H 0 1C 0 0 0 0 0 0 0 0 0 0 0 2C,6H 2C,2H 2C,2H 0 0     0 0 0 Nutsedge 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2G 0 0 0 0 0 0 0 Rice 4G 2G     4G 0 2C,3G 0 0 0 0 0 5H 0 3G 0 9H 8H 3C,6H 0 8H 0 0 0 Sorghum 2G 0 3C,5G     0 2G 0 0 0 0 0 2C,4G 0 2C,5G 0 9H 2G 3C,6H 0 3G 0 2G 0 Soybean 2C,2H 2G     2C,2H 0 2C 0 0 0 0 0 1H 0 0 0 3C,3H 1C 2C 0 0 0 1H 0 Sugar beet 5G 2G 1H     0 7G 2G 0 0 2G 0 4G 0 0 0 1C 0 0 0 0 0 0 0 Velvetleaf 5G 0 1H 0 0 0 0 0     0 0 3G 0 0 0 5H 0 0 0 2G 0 0 0 Wheat 0 0 0 0 0 0 0 0 0 0 0 0 2G 0 5H 0     5G 0 0 0 0 0 Wild oat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2C,3G 0 2G 0 0 0 0

TEST B

Seeds of barley (Hordeum vulgare), barnyardgrass (Echinochloacrus-galli), blackgrass (Alopecurus myosuroides), chickweed (Stellariamedia), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton(Gossypium hirsutum), crabgrass (Digitaria spp.), downy brome (Bromustectorum), giant foxtail (Setaria faberi), green foxtail (Setariaviridis), jimsonweed (Datura stramonium), johnsongrass (Sorghumhalepense), lambsquarters (Chenopodium album), morningglory (Ipomoeaspp.), rape (Brassica napus), rice (Oryza sativa), sicklepod (Cassiaobtusifolia), soybean (Glycine max), sugar beet (Beta vulgaris), teaweed(Sida spinosa), velvetleaf (Abutilon theophrasti), wheat (Triticumaestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avenafatua) and purple nutsedge (Cyperus rotundus) tubers were planted andtreated preemergence with test chemicals dissolved in a non-phytotoxicsolvent. At the same time, these crop and weed species were also treatedwith postemergence applications of test chemicals. Plants ranged inheight from two to eighteen cm (two to three leaf stage) forpostemergence treatments. Treated plants and controls were maintained ina greenhouse for approximately 24 days, after which all species werecompared to controls and visually evaluated. The ratings, summarized inTable B, are based on a scale of 0 to 100 where 0 is no effect and 100is complete control. A dash (-) response means no test result.

    TABLE B      POSTEMERGENCE Cmpd 3 Cmpd 7 Cmpd 13 Cmpd 19 Cmpd 31 RATE (g/ha) 62 16 4 1      250 62 16 4 500 250 125 62 250 62 16 4 250 62 16 4       Barley 90 70 50 30 80 60 30  0 60 60 60 60 60 60 60 60 70 60 60 60     Barnyardgrass 90 80 70 50 100  90 80 70 100  100  95 90 100  95 90 60     100  90 85 80 Blackgrass 60 50 40  0  0  0  0  0 70 60 50 40 90 70 50 30     70 60 40 30 Chickweed 60 30  0  0 80 80 30 20 90 80 70 60 100  90 70 50     90 70 50 30 Cocklebur 90 70 50 30 100  100  90 40 100  100  90 80 90 80     70 50 90 80 75 70 Corn 70 50 30  0 100   100  100  60 100  100  100  70     100  70 60 50 80 70 60 50 Cotton 70 60 50 40 100  95 90 60 100  100  90     80 100  90 80 40 100  90 60 40 Crabgrass 30  0  0  0 45 40  0  0 70 60     30  0 60 30  0  0 70 50 30  0 Downy brome 80 50 30  0 50 20 20  0 70 50     40 40 60 50 40 30 60 50 40 30 Giant foxtail 90 80 70 50 100  100  90 40     90 70 60 60 100  100  100  70 80 70 30  0 Green foxtail 90 70 50 30 90     80 70 40 70 70 70 70 100  90 80 30 80 70 40  0 Jimsonweed 100  50 40 30     -- 50 20  0 90 60 50 40 70 50 40 30 70 60 50 40 Johnsongrass 70 50 30  0     70 60 50 20 100  100  90 80 95 90 40 30 90 80 70 60 Lambsquarters 80 70     60 50 90 80 30  0 100  100  90 60 100  80 70 50 100  100       70 40 Morningglory 70 60 30  0 85 85 40 30 90 80 70 60 100  90 60 40     100  80 70 40 Nutsedge 70 50 30  0 75 50 50  0 60 50 50 50 70 60 30  0     100  70 50 40 Rape 100  100  100  70 100  100  85 80 100  100  100  100     100  100  100  100  100  100  100  90 Rice 90 70 50 30 100  100  95 90     100  90 80 60 100  90 80 70 90 80 70 60 Sicklepod 60 30  0  0 40 40 35     0 60 40 20  0 90 60 30  0 70 30  0  0 Soybean 70 50 30  0 60 55 40 30 95     90 80 80 100  90 80 60 70 65 40 30 Sugar beet 60 30  0  0 40 35 30  0 90     70 50 30 100  100  90 60 70 60 40 30 Teaweed 90 70 60 50 85 60 40 30 100      90 85 80 100  90 70 50 95 90 70 40 Velvetleaf 100  80 50 30 100  100     60 50 100  100  100  100  100  100  100  100  95 90 70 60 Wheat 70 50 30      0 30 20  0  0 60 50 50 50 60 60 40 20 50 40 40 30 Wild buckwheat 90 60     30  0 100  50 50 50 95 90 80 70 95 90 80 60 100  75 70 50 Wild oat 70 50      0  0  0  0  0  0 60 50 40 30 60 50 40 30 70 50 30      0                      PREEMERGENCE Cmpd 3 Cmpd 7 Cmpd 13 Cmpd 19 Cmpd     31 RATE (kg/ha) 62 16 4 1 250 62 16 4 500 250 125 62 250 62 16 4 250 62     16 4       Barley 70 50  0  0 40 20  0  0 80 75 70 60 70 60 50 40 80 80 60 30     Barnyardgrass 100  90 60 30 95 90 40  0 100  100  90 85 100  90 60 30     100  100  70 30 Blackgrass 100  80 50 30 50 30  0  0 90 80 70 60 90 80     70 50 60 50 50 30 Chickweed 90 80 70 50 30 30 30 30 90 80 70 60 95 90 70     60 90 80 50 30 Cocklebur 90 70 50 30 60 40  0  0 100  90 85 80 90 80 75     70 100  90 -- -- Corn 90 60  0  0 80 80  0  0 95 90 85 80 100  80 30  0     100  90 70  0 Cotton 90 60 30  0 40 40  0  0 80 70 60 40 80 50 30  0 100      90 50 40 Crabgrass 100  90 70 60 80 50  0  0 90 85 80 75 100  90 80 70     80 70 60 50 Downy brome 80 50 30  0  0  0  0  0 90 80 70 60 80 50 30  0     100  90 70 40 Giant foxtail 100  100  80 70 80 30  0  0 95 90 80 70 100     90 80 50 100  70 60  0 Green foxtail 100  100  70 50 100  80 30  0 90 80     70 60 100  90 80 40 100  100  70 40 Jimsonweed 70 50 30  0 50 30  0  0     90 70 50 30 90 70 50 30 40  0  0  0 Johnsongrass 100  90 60 30 80  0  0     0 90 85 80 75 90 80 50  0 100  80 20  0 Lambsquarters 60 30  0  0 70 50     0  0 100  100  95 90 95 90 80 70 100  80 80 50 Morningglory 90 80 70 50     70 40 30 20 90 80 75 70 80 50 40 30 100  90 70  0 Nutsedge 70 50 30  0     0  0  0  0 90 80 70 60 100  80 50 30 90 60 60 50 Rape 90 60 30  0 90 70     30  0 90 85 80 75 90 80 40 30 100  100  100   0 Rice 90 80 70 50 100     100  100  40 100  100  100  100  100  100  90 60 100  90 70 30 Sicklepod     70 60 50 40 40 30  0  0 40 30 20  0 90 40  0  0 100  -- 80 80 Soybean 90     60 30  0 60  0  0  0 50 30 20  0 60 30  0  0 70 20  0  0 Sugar beet 30     20  0  0  0  0  0  0 90 80 70 60 90 70 60 50 80 50 30 20 Teaweed 80 70     50 30 50 30  0  0 90 80 75 70 95 90 80 -- 100  100  100  50 Velvetleaf     80 70 60 30 80 50 -- -- 100  100  90 40 90 80 30  0 80  0  0  0 Wheat 60     30  0  0 30  0  0  0 80 60 50 40 80 70 50 40 60 60 50 30 Wild buckwheat     70 50 30  0 70 50 30  0 90 80 75 70 90 80 75 70 100  100  90 80 Wild oat     70 50 30  0  0  0  0  0 70 60 50 30 70 50 30      0 60 50 30 30

TEST C

Seeds selected from blackgrass (Alopecurus myosuroides), catchweedbedstraw (Galium aparine), chickweed (Stellaria media), knotweed(Polygonum aviculare), lambsquarters (Chenopodium album), Persianspeedwell (Veronica persica), scentless chamomille (Matricaria inodora),sugar beet (Beta vulgaris), viola (Viola arvensis), wheat (Triticumaestivum), wild buckwheat (Polygonum convolvulus), and wild oat (Avenafatua) were planted and treated preemergence with test chemicalsdissolved in a non-phytotoxic solvent. Selected species from this listof crops and weeds were also treated with postemergence applications oftest chemicals. Plants ranged in height from two to twenty cm (two tothree leaf stage) for postemergence treatments. Treated plants andcontrols were maintained in a greenhouse for approximately 24 days,after which all species were compared to controls and visuallyevaluated. The ratings, summarized in Table C, are based on a scale of 0to 100 where 0 is no effect and 100 is complete control. A dash (-)response means no test result.

                                      TABLE C                                     __________________________________________________________________________               Cmpd 1     Cmpd 2     Cmpd 3                                       RATE (g/ha)                                                                              125                                                                              64                                                                              32                                                                              16                                                                              8 125                                                                              64                                                                              32                                                                              16                                                                              8 64 32 16 8 4                                 __________________________________________________________________________    POSTEMERGENCE                                                                 Blackgrass 0  0 0 0 0 0  0 0 0 0 50 50 30 20                                                                              0                                 Catchweed bedstraw                                                                       0  0 0 0 0 0  0 0 0 0 100                                                                              100                                                                              100                                                                              50                                                                              0                                 Chickweed  0  0 0 0 0 0  0 0 0 0 80 80 20 0 0                                 Knotweed   0  0 0 0 0 0  0 0 0 0 -- -- -- --                                                                              --                                Lambsquarters                                                                            0  0 0 0 0 0  0 0 0 0 0  0  0  0 0                                 Persian speedwell                                                                        0  0 0 0 0 0  0 0 0 0 0  0  0  0 0                                 Scentless chamomille                                                                     0  0 0 0 0 0  0 0 0 0 100                                                                              90 90 90                                                                              50                                Sugar beet 0  0 0 0 0 0  0 0 0 0 20 10 0  0 0                                 Viola      0  0 0 0 0 0  0 0 0 0 90 50 50 50                                                                              50                                Wheat      0  0 0 0 0 0  0 0 0 0 70 50 50 50                                                                              30                                Wild buckwheat                                                                           0  0 0 0 0 0  0 0 0 0 90 90 75 50                                                                              30                                Wild oat   20 0 0 0 0 0  0 0 0 0 50 50 50 30                                                                              0                                 RATE (g/ha)                      64 32 16 8 4                                 PREEMERGENCE                                                                  Blackgrass                       90 -- -- --                                                                              50                                Catchweed bedstraw               80 -- -- --                                                                              80                                Chickweed                        30 -- -- --                                                                              0                                 Knotweed                         100                                                                              -- -- --                                                                              100                               Lambsquarters                    -- -- -- --                                                                              --                                Persian speedwell                0  -- -- --                                                                              0                                 Scentless chamomille             90 -- -- --                                                                              80                                Sugar beet                       20 -- -- --                                                                              0                                 Viola                            80 -- -- --                                                                              20                                Wheat                            80 -- -- --                                                                              20                                Wild buckwheat                   100                                                                              -- -- --                                                                              70                                Wild oat                         100                                                                              -- -- --                                                                              30                                __________________________________________________________________________                        Cmpd 5      Cmpd 7                                                 RATE (g/ha)                                                                              125                                                                              64                                                                              32                                                                              16                                                                              8  250 125                                                                              64 32                                                                              16                                __________________________________________________________________________             POSTEMERGENCE                                                                 Blackgrass 30 30                                                                              30                                                                              30                                                                              0  40  30 0  0 0                                          Catchweed bedstraw                                                                       50 40                                                                              0 0 0  100 80 80 50                                                                              0                                          Chickweed  0  0 0 0 0  50  30 30 30                                                                              0                                          Knotweed   70 70                                                                              50                                                                              0 0  --  -- -- --                                                                              --                                         Lambsquarters                                                                            0  0 0 0 0  --  30 0  0 0                                          Persian speedwell                                                                        50 30                                                                              0 0 0  0   0  0  0 0                                          Scentless chamomille                                                                     60 0 0 0 0  100 90 80 80                                                                              80                                         Sugar beet 40 40                                                                              30                                                                              20                                                                              0  10  10 0  0 0                                          Viola      40 20                                                                              20                                                                              20                                                                              0  40  30 0  0 0                                          Wheat      30 20                                                                              20                                                                              20                                                                              20 50  30 30 30                                                                              0                                          Wild buckwheat                                                                           50 0 0 0 0  100 90 80 70                                                                              70                                         Wild oat   30 30                                                                              30                                                                              30                                                                              0  30  30 20 20                                                                              0                                          RATE (g/ha)            250 125                                                                              64 32                                                                              16                                         PREEMERGENCE                                                                  Blackgrass             30  30 0  0 0                                          Catchweed bedstraw     0   0  0  0 0                                          Chickweed              0   0  0  0 0                                          Knotweed               --  -- -- --                                                                              0                                          Lambsquarters          100 100                                                                              90 0 0                                          Persian speedwell      0   0  0  0 0                                          Scentless chamomille   --  -- -- --                                                                              --                                         Sugar beet             0   0  0  0 0                                          Viola                  30  0  0  0 0                                          Wheat                  30  0  0  0 0                                          Wild buckwheat         40  0  0  0 0                                          Wild oat               40  0  0  0 0                                 __________________________________________________________________________                        Cmpd 13      Cmpd 15                                               RATE (g/ha)                                                                              64  32 16  8 125 64                                                                              32 16                                                                              8                                 __________________________________________________________________________             POSTEMERGENCE                                                                 Blackgrass 0   0  0   0 0   0 0  0 0                                          Catchweed bedstraw                                                                       0   0  0   0 0   0 0  0 0                                          Chickweed  20  0  0   --                                                                              0   0 0  0 0                                          Knotweed   --  -- --  0 --  --                                                                              -- --                                                                              --                                         Lambsquarters                                                                            100 100                                                                              100 50                                                                              --  --                                                                              -- --                                                                              --                                         Persian speedwell                                                                        50  50 30  30                                                                              100 0 0  0 0                                          Scentless chamomille                                                                     100 100                                                                              70  30                                                                              0   0 0  0 0                                          Sugar beet 0   0  0   0 30  20                                                                              0  0 0                                          Viola      0   0  0   0 --  0 0  0 0                                          Wheat      20  20 0   0 40  40                                                                              40 0 0                                          Wild buckwheat                                                                           80  70 0   0 100 0 0  0 0                                          Wild oat   30  30 20  0 30  0 0  0 0                                          PREEMERGENCE                                                                  Blackgrass     0  0     0   0 0                                               Catchweed bedstraw                                                                           30 0     70  30                                                                              0                                               Chickweed      0  0     90  70                                                                              30                                              Knotweed       -- --    80  --                                                                              --                                              Lambsquarters  0  --    --  --                                                                              --                                              Persian speedwell                                                                            0  0     50  50                                                                              0                                               Scentless chamomille                                                                         0  0     20  20                                                                              0                                               Sugar beet     0  0     100 80                                                                              10                                              Viola          90 0     60  30                                                                              20                                              Wheat          20 0     80  60                                                                              50                                              Wild buckwheat 50 40    80  50                                                                              0                                               Wild oat       0  0     30  0 0                                      __________________________________________________________________________                        Cmpd 19     Cmpd 31                                                RATE (g/ha)                                                                              32 16 8  4  250                                                                              125                                                                              64 32 16                                __________________________________________________________________________             POSTEMERGENCE                                                                 Blackgrass 50 50 30 0  50 50 50 50 50                                         Catchweed bedstraw                                                                       90 90 70 0  100                                                                              100                                                                              70 30 30                                         Chickweed  100                                                                              90 70 30 80 70 50 50 50                                         Knotweed   -- -- -- -- -- -- -- -- --                                         Lambsquarters                                                                            100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                        Persian speedwell                                                                        30 0  0  0  0  0  0  0  0                                          Scentless chamomille                                                                     80 80 40 0  90 90 90 70 50                                         Sugar beet 90 50 50 30 80 50 10 0  0                                          Viola      30 0  0  0  80 30 30 30 0                                          Wheat      60 50 40 20 70 70 70 30 30                                         Wild buckwheat                                                                           100                                                                              100                                                                              0  0  100                                                                              100                                                                              90 70 50                                         Wild oat   30 30 0  0  50 40 40 40 20                                         RATE (g/ha)                                                                              125                                                                              64 32 16                                                        PREEMERGENCE                                                                  Blackgrass 80 70 70 70 70 70 30 30 0                                          Catchweed bedstraw                                                                       100                                                                              80 80 30 70 50 20 0  0                                          Chickweed  100                                                                              100                                                                              90 90 0  0  0  0  0                                          Knotweed   100                                                                              100                                                                              100                                                                              100                                                                              -- -- -- -- --                                         Lambsquarters                                                                            100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              90 90                                         Persian speedwell                                                                        70 40 0  0  0  0  0  0  0                                          Scentless chamomille                                                                     100                                                                              90 90 90 -- -- -- -- --                                         Sugar beet 90 90 80 80 0  0  0  0  0                                          Viola      90 90 90 80 40 30 30 30 0                                          Wheat      80 50 30 10 50 40 30 30 30                                         Wild buckwheat                                                                           90 90 90 50 100                                                                              80 40 30 30                                         Wild oat   70 60 30 30 40 40 30 0  0                                 __________________________________________________________________________

What is claimed is:
 1. A compound of the formula: ##STR37## wherein R isH or CH₃ ;R₁ is NO₂, CO₂ R₄, C(O)R₅, S(O)₂ R₆, ##STR38## R₂ is ##STR39##or CHO; R₃ is H, OCH₃, CH₃ or Cl; R₄ is C₁ -C₃ alkyl, C₂ -C₄alkoxyalkyl, C₂ -C₃ haloalkyl, allyl or propargyl; R₅ is C₁ -C₃ alkyl,C₂ -C₄ alkoxyalkyl, C₃ -C₄ cycloalkyl or cyclopropylmethyl; R₆ is C₁ -C₃alkyl or C₂ -C₄ alkoxyalkyl; R₇ is C₁ -C₃ alkyl, C₂ -C₄ alkoxyalkyl, C₃-C₄ cycloalkyl, cyclopropylmethyl, C₁ -C₂ alkoxy, CN or Cl; R₈ is C₁ -C₃alkyl; R₉ and R₁₀ are independently C₁ -C₂ alkyl; R₁₁ is H or CH₃ ; R₁₂is H or CH₃ ; R₁₃ is CN, SCN, NH₂, NHCH₃, N(CH₃)₂, NHC(O)CH₃ or W₂ R₁₆ ;R₁₄ is C₁ -C₃ alkyl, C₂ -C₄ alkoxyalkyl or C₂ -C₃ haloalkyl; R₁₅ is H,C₁ -C₃ alkyl, C₂ -C₄ alkoxyalkyl or C₂ -C₃ haloalkyl; R₁₆ is H, C₁ -C₆alkyl, C₃ -C₄ cycloalkyl or C₄ -C₅ cycloalkylalkyl; W₂ is O or S; X isC₁ -C₂ alkyl, OCH₃, Cl, or OCF₂ H; Y is H, CH₃, C₁ -C₂ alkoxy, NHCH₃, orN(CH₃)₂ ; and Z is CH;and their agriculturally suitable salts; providedthat 1) when X is Cl, then Y is OCH₃, OC₂ H₅, NHCH₃, or N(CH₃)₂ ; 2)when X is OCF₂ H, then R₂ is ##STR40## 3) when R₂ is ##STR41## then R₁is CO₂ R₄ ; 4) When R₁₆ is H, W₂ is O.
 2. A compound of claim 1 whereinRis H and R₃ is H.
 3. A compound of claim 2 whereinR₄ is CH₃, CH₂ CH₃ orCH₂ OCH₃ ; R₅ is C₁ -C₃ alkyl, cyclopropyl, cyclopropylmethyl or CH₂OCH₃ ; R₆ is C₁ -C₃ alkyl or CH₂ OCH₃ ; R₇ is C₁ -C₃ alkyl, cyclopropyl,cyclopropylmethyl or CH₂ OCH₃ ; and R₁₆ is H or C₁ -C₃ alkyl.
 4. Thecompound of claim 1 which is methyl2-[[[[(4,6-dimethoxypyrimidin-2-yl)amino]carbonyl]amino]sulfonyl]-5-(methoxymethyl)benzoate.5. The compound of claim 1 which is methyl2-[[[[(4,6-dimethoxypyrimidin-2-yl)amino]carbonyl]amino]sulfonyl]-5-(hydroxymethyl)benzoate.6. A compound of claim 3 where R₂ is ##STR42##
 7. A compound of claim 6where R₁₃ is W₂ R₁₆.
 8. A compound of claim 3 where R₂ is NHR₁₄.
 9. Acompound of claim 3 where R₂ is ##STR43##
 10. A compound of claim 3where R₂ is CHO.
 11. A composition suitable for controlling the growthof undesired vegetation which comprises an effective amount of acompound of claim 1 and at least one of the following: surfactant, soliddiluent or liquid diluent.
 12. A composition suitable for controllingthe growth of undesired vegetation which comprises an effective amountof a compound of claim 2 and at least one of the following: surfactant,solid diluent or liquid diluent.
 13. A composition suitable forcontrolling the growth of undesired vegetation which comprises aneffective amount of a compound of claim 3 and at least one of thefollowing: surfactant, solid diluent or liquid diluent.
 14. Acomposition suitable for controlling the growth of undesired vegetationwhich comprises an effective amount of a compound of claim 4 and atleast one of the following: surfactant, solid diluent or liquid diluent.15. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 5and at least one of the following: surfactant, solid diluent or liquiddiluent.
 16. A composition suitable for controlling the growth ofundesired vegetation which comprises an effective amount of a compoundof claim 6 and at least one of the following: surfactant, solid diluentor liquid diluent.
 17. A composition suitable for controlling the growthof undesired vegetation which comprises an effective amount of acompound of claim 7 and at least one of the following: surfactant, soliddiluent or liquid diluent.
 18. A composition suitable for controllingthe growth of undesired vegetation which comprises an effective amountof a compound of claim 8 and at least one of the following: surfactant,solid diluent or liquid diluent.
 19. A composition suitable forcontrolling the growth of undesired vegetation which comprises aneffective amount of a compound of claim 9 and at least one of thefollowing: surfactant, solid diluent or liquid diluent.
 20. Acomposition suitable for controlling the growth of undesired vegetationwhich comprises an effective amount of a compound of claim 10 and atleast one of the following: surfactant, solid diluent or liquid diluent.21. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 1. 22. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 2. 23. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound of claim3.
 24. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 4. 25. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 5. 26. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound of claim6.
 27. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 7. 28. A method for controlling undesired vegetationin sugarbeets which comprises applying to the locus of the sugarbeets aneffective amount of the compound of claim
 4. 29. A method forcontrolling undesired vegetation in sugarbeets which comprises applyingto the locus of the sugarbeets an effective amount of the compound ofclaim
 5. 30. A method for controlling undesired vegetation in sugarbeetswhich comprises applying to the locus of the sugarbeets an effectiveamount of the compound of claim
 6. 31. A method for controllingundesired vegetation in sugarbeets which comprises applying to the locusof the sugarbeets an effective amount of the compound of claim
 7. 32. Amethod for controlling undesired vegetation in sugarbeets whichcomprises applying to the locus of the sugarbeets an effective amount ofthe compound of claim
 8. 33. A method for controlling undesiredvegetation in sugarbeets which comprises applying to the locus of thesugarbeets an effective amount of the compound of claim
 9. 34. A methodfor controlling undesired vegetation in sugarbeets which comprisesapplying to the locus of the sugarbeets an effective amount of thecompound of claim 10.